IL105623A - Oxazaborolidine Catalysts for Anantyslective Reduction of Prochiral Ketones - Google Patents
Oxazaborolidine Catalysts for Anantyslective Reduction of Prochiral KetonesInfo
- Publication number
- IL105623A IL105623A IL105623A IL10562393A IL105623A IL 105623 A IL105623 A IL 105623A IL 105623 A IL105623 A IL 105623A IL 10562393 A IL10562393 A IL 10562393A IL 105623 A IL105623 A IL 105623A
- Authority
- IL
- Israel
- Prior art keywords
- phenyl
- oxazaborolidine
- borane
- alkyl
- chiral
- Prior art date
Links
- 150000002576 ketones Chemical class 0.000 title claims abstract description 32
- BDOLXPFAFMNDOK-UHFFFAOYSA-N oxazaborolidine Chemical compound B1CCON1 BDOLXPFAFMNDOK-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 239000003054 catalyst Substances 0.000 title abstract description 17
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910000085 borane Inorganic materials 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000003638 chemical reducing agent Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- -1 (Cj-C^alkyl Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000011065 in-situ storage Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- FVQDOKQWEOZEBQ-UHFFFAOYSA-N B1NCCO1 Chemical compound B1NCCO1 FVQDOKQWEOZEBQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract description 10
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 238000006722 reduction reaction Methods 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000008363 phosphate buffer Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- BRTALTYTFFNPAC-UHFFFAOYSA-N boroxin Chemical compound B1OBOBO1 BRTALTYTFFNPAC-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- GEJJWYZZKKKSEV-UONOGXRCSA-N (1r,2s)-2-amino-1,2-diphenylethanol Chemical compound C1([C@@H](O)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 GEJJWYZZKKKSEV-UONOGXRCSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- GEJJWYZZKKKSEV-KGLIPLIRSA-N (1s,2r)-2-amino-1,2-diphenylethanol Chemical compound C1([C@H](O)[C@H](N)C=2C=CC=CC=2)=CC=CC=C1 GEJJWYZZKKKSEV-KGLIPLIRSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GBBSAMQTQCPOBF-UHFFFAOYSA-N 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane Chemical compound CB1OB(C)OB(C)O1 GBBSAMQTQCPOBF-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- XWCQSILTDPAWDP-QMMMGPOBSA-N (1r)-2-chloro-1-phenylethanol Chemical compound ClC[C@H](O)C1=CC=CC=C1 XWCQSILTDPAWDP-QMMMGPOBSA-N 0.000 description 1
- FVOOPOSZDXPIMS-SECBINFHSA-N (2r)-3,4-dihydro-2h-chromen-2-ol Chemical compound C1=CC=C2O[C@@H](O)CCC2=C1 FVOOPOSZDXPIMS-SECBINFHSA-N 0.000 description 1
- FVOOPOSZDXPIMS-VIFPVBQESA-N (2s)-3,4-dihydro-2h-chromen-2-ol Chemical compound C1=CC=C2O[C@H](O)CCC2=C1 FVOOPOSZDXPIMS-VIFPVBQESA-N 0.000 description 1
- MGSHXMOLUWTMGP-QMMMGPOBSA-N (4s)-3,4-dihydro-2h-chromen-4-ol Chemical compound C1=CC=C2[C@@H](O)CCOC2=C1 MGSHXMOLUWTMGP-QMMMGPOBSA-N 0.000 description 1
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- VOXXGUAZBWSUSS-UHFFFAOYSA-N 2,4,6-triphenyl-1,3,5,2,4,6-trioxatriborinane Chemical compound O1B(C=2C=CC=CC=2)OB(C=2C=CC=CC=2)OB1C1=CC=CC=C1 VOXXGUAZBWSUSS-UHFFFAOYSA-N 0.000 description 1
- UAXQBCQWFKWRTA-UHFFFAOYSA-N 2-bromo-1-[2-(trifluoromethyl)-1,3-thiazol-4-yl]ethanone Chemical compound FC(F)(F)C1=NC(C(=O)CBr)=CS1 UAXQBCQWFKWRTA-UHFFFAOYSA-N 0.000 description 1
- LRRQSCPPOIUNGX-UHFFFAOYSA-N 2-hydroxy-1,2-bis(4-methoxyphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1C(O)C(=O)C1=CC=C(OC)C=C1 LRRQSCPPOIUNGX-UHFFFAOYSA-N 0.000 description 1
- HOEFKWVMQYMLHU-UHFFFAOYSA-N 2-hydroxyimino-1,2-bis(4-methoxyphenyl)ethanol Chemical compound C1=CC(OC)=CC=C1C(O)C(=NO)C1=CC=C(OC)C=C1 HOEFKWVMQYMLHU-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001543 aryl boronic acids Chemical class 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 238000007193 benzoin condensation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 125000005620 boronic acid group Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 101150091502 ced-6 gene Proteins 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011982 enantioselective catalyst Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88331792A | 1992-05-14 | 1992-05-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL105623A0 IL105623A0 (en) | 1993-09-22 |
| IL105623A true IL105623A (en) | 1998-02-22 |
Family
ID=25382382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL105623A IL105623A (en) | 1992-05-14 | 1993-05-06 | Oxazaborolidine Catalysts for Anantyslective Reduction of Prochiral Ketones |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5552548A (no) |
| EP (1) | EP0640089B1 (no) |
| JP (1) | JP2525127B2 (no) |
| KR (2) | KR0149208B1 (no) |
| AT (1) | ATE146790T1 (no) |
| AU (1) | AU659929B2 (no) |
| CA (1) | CA2134096C (no) |
| DE (1) | DE69306945T2 (no) |
| DK (1) | DK0640089T3 (no) |
| ES (1) | ES2096275T3 (no) |
| FI (1) | FI107259B (no) |
| GR (1) | GR3022171T3 (no) |
| HU (1) | HU215089B (no) |
| IL (1) | IL105623A (no) |
| MX (1) | MX9302785A (no) |
| MY (1) | MY111251A (no) |
| NO (1) | NO300500B1 (no) |
| NZ (1) | NZ249302A (no) |
| TW (1) | TW232696B (no) |
| WO (1) | WO1993023408A1 (no) |
| ZA (1) | ZA933340B (no) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06329679A (ja) * | 1993-01-20 | 1994-11-29 | Nissan Chem Ind Ltd | 光学活性β−アミノアルコキシボラン錯体 |
| TW416958B (en) * | 1993-05-14 | 2001-01-01 | Pfizer | Enantioselective oxazaborolidine catalysts |
| JPH08507310A (ja) * | 1993-07-16 | 1996-08-06 | ファイザー・インク． | チアゾール誘導体のエナンチオ選択的調製 |
| DK0724552T3 (da) * | 1993-11-30 | 1997-12-22 | Pfizer | Fremgangsmåde til fremstilling af chiralt tetralon |
| US5495054A (en) * | 1994-05-31 | 1996-02-27 | Sepracor, Inc. | Tetrahydroindeno[1,2-D][1,3,2]oxazaboroles and their use as enantioselective catalysts |
| WO1998012155A1 (fr) * | 1996-09-18 | 1998-03-26 | Shionogi & Co., Ltd. | Procede de preparation d'un alcool actif sur plan optique faisant appel a une reduction a l'aide de borane asymetrique |
| ES2130083B1 (es) * | 1997-08-04 | 2000-01-16 | Esteve Labor Dr | Procedimiento para la obtencion de los enantiomeros de cizolirtina. |
| US6509472B2 (en) * | 2000-09-11 | 2003-01-21 | Schering Corporation | 4-Cyclohexyl-1,3,2-oxazaborolidine chiral accessories |
| DE602007008564D1 (en) * | 2006-06-26 | 2010-09-30 | Basf Se | Boranetherkomplexe |
| EP2139845A1 (en) * | 2007-02-26 | 2010-01-06 | Teva Pharmaceutical Industries Ltd. | Intermediates and processes for the synthesis of ramelteon |
| US7838691B2 (en) * | 2007-04-05 | 2010-11-23 | Board Of Regents, Of The University Of Texas System | Palmerolides: methods of preparation and derivatives thereof |
| EP2152074A4 (en) * | 2007-04-30 | 2011-07-27 | Adolor Corp | (-) - E-10-OH-NT COMPOSITIONS, METHODS OF SYNTHESIS AND USE |
| US8084630B2 (en) * | 2007-05-31 | 2011-12-27 | Teva Pharmaceutical Industries Ltd. | Process for the synthesis of ramelteon and its intermediates |
| US20090082568A1 (en) * | 2007-09-21 | 2009-03-26 | Basf Aktiengesellschaft | Accelerated reduction of organic substances with boranes |
| WO2009056993A2 (en) * | 2007-11-01 | 2009-05-07 | Teva Pharmaceutical Industries Ltd. | A process for the synthesis of ramelteon and its intermediates |
| WO2010045565A1 (en) * | 2008-10-16 | 2010-04-22 | Teva Pharmaceutical Industries Ltd. | Process for the synthesis of ramelteon and its intermediates |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4943635A (en) * | 1987-08-27 | 1990-07-24 | President & Fellows Of Harvard College | Enantioselective reduction of ketones |
| US5039802A (en) * | 1990-04-18 | 1991-08-13 | Merck & Co., Inc. | Arylation process for preparation of chiral catalysts for ketone reduction |
| US5157129A (en) * | 1990-04-18 | 1992-10-20 | Merck & Co., Inc. | Enantiospecific synthesis of s-(+)-5,6-dihydro-4-(r-amino)-4h-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide |
| JPH06329679A (ja) * | 1993-01-20 | 1994-11-29 | Nissan Chem Ind Ltd | 光学活性β−アミノアルコキシボラン錯体 |
| TW416958B (en) * | 1993-05-14 | 2001-01-01 | Pfizer | Enantioselective oxazaborolidine catalysts |
-
1993
- 1993-02-01 AU AU35931/93A patent/AU659929B2/en not_active Ceased
- 1993-02-01 DK DK93904636.3T patent/DK0640089T3/da active
- 1993-02-01 ES ES93904636T patent/ES2096275T3/es not_active Expired - Lifetime
- 1993-02-01 CA CA002134096A patent/CA2134096C/en not_active Expired - Fee Related
- 1993-02-01 JP JP5520175A patent/JP2525127B2/ja not_active Expired - Fee Related
- 1993-02-01 AT AT93904636T patent/ATE146790T1/de not_active IP Right Cessation
- 1993-02-01 KR KR1019940704055A patent/KR0149208B1/ko active
- 1993-02-01 KR KR1019940704055A patent/KR950701637A/ko not_active IP Right Cessation
- 1993-02-01 NZ NZ249302A patent/NZ249302A/en unknown
- 1993-02-01 EP EP93904636A patent/EP0640089B1/en not_active Expired - Lifetime
- 1993-02-01 WO PCT/US1993/000687 patent/WO1993023408A1/en active IP Right Grant
- 1993-02-01 DE DE69306945T patent/DE69306945T2/de not_active Expired - Fee Related
- 1993-02-13 TW TW082101021A patent/TW232696B/zh active
- 1993-05-06 IL IL105623A patent/IL105623A/en not_active IP Right Cessation
- 1993-05-12 MX MX9302785A patent/MX9302785A/es unknown
- 1993-05-13 FI FI932174A patent/FI107259B/fi not_active IP Right Cessation
- 1993-05-13 ZA ZA933340A patent/ZA933340B/xx unknown
- 1993-05-13 HU HU9301395A patent/HU215089B/hu not_active IP Right Cessation
- 1993-05-14 MY MYPI93000900A patent/MY111251A/en unknown
-
1994
- 1994-10-13 US US08/318,828 patent/US5552548A/en not_active Expired - Fee Related
- 1994-11-11 NO NO944297A patent/NO300500B1/no not_active IP Right Cessation
-
1996
- 1996-12-30 GR GR960403546T patent/GR3022171T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO300500B1 (no) | 1997-06-09 |
| DE69306945T2 (de) | 1997-05-07 |
| NZ249302A (en) | 1996-11-26 |
| FI932174A (fi) | 1993-11-15 |
| KR0149208B1 (ko) | 1998-10-15 |
| AU659929B2 (en) | 1995-06-01 |
| EP0640089A1 (en) | 1995-03-01 |
| ZA933340B (en) | 1994-11-14 |
| IL105623A0 (en) | 1993-09-22 |
| ES2096275T3 (es) | 1997-03-01 |
| CA2134096C (en) | 1997-11-25 |
| MY111251A (en) | 1999-10-30 |
| NO944297D0 (no) | 1994-11-11 |
| TW232696B (no) | 1994-10-21 |
| HUT65136A (en) | 1994-04-28 |
| DE69306945D1 (de) | 1997-02-06 |
| DK0640089T3 (da) | 1997-06-16 |
| JP2525127B2 (ja) | 1996-08-14 |
| US5552548A (en) | 1996-09-03 |
| WO1993023408A1 (en) | 1993-11-25 |
| KR950701637A (ko) | 1995-04-28 |
| FI107259B (fi) | 2001-06-29 |
| FI932174A0 (fi) | 1993-05-13 |
| GR3022171T3 (en) | 1997-03-31 |
| EP0640089B1 (en) | 1996-12-27 |
| HU215089B (hu) | 1998-09-28 |
| NO944297L (no) | 1994-11-11 |
| ATE146790T1 (de) | 1997-01-15 |
| HU9301395D0 (en) | 1993-09-28 |
| CA2134096A1 (en) | 1993-11-25 |
| JPH07503734A (ja) | 1995-04-20 |
| AU3593193A (en) | 1993-12-13 |
| MX9302785A (es) | 1994-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IL105623A (en) | Oxazaborolidine Catalysts for Anantyslective Reduction of Prochiral Ketones | |
| Bolm et al. | Optically active bipyridines in nickel catalyzed enantioselective conjugate addition to enones | |
| KR0180262B1 (ko) | 거울상선택적 옥사자보로리딘 촉매 | |
| Asami et al. | Enantioselective addition of dialkylzinc to aldehydes catalyzed by (S)-2-(N, N-disubstituted aminomethyl) indoline | |
| Moberg | Molybdenum-catalyzed and tungsten-catalyzed enantioselective allylic substitutions | |
| Braga et al. | Catalytic enantioselective aryl transfer: asymmetric addition of boronic acids to aldehydes using pyrrolidinylmethanols as ligands | |
| Liu et al. | Allylboration of ketones and imines with a highly reactive bifunctional allyl pinacolatoboronate reagent | |
| Widhalm et al. | Chiral ferrocene derivatives containing a 2, 2′-bridged binaphthyl moiety | |
| US5495054A (en) | Tetrahydroindeno[1,2-D][1,3,2]oxazaboroles and their use as enantioselective catalysts | |
| Yu et al. | A convenient approach to difluoromethylated all-carbon quaternary centers via Ni (II)-catalyzed enantioselective Michael addition | |
| Yadav et al. | Efficient synthesis of optically active 2-azido-1-arylethanols via oxazaborolidine-catalysed asymmetric borane reduction | |
| Li et al. | Remote substituent effect in palladium/pyridinyl-oxazolines catalyzed asymmetric allylic alkylation | |
| Cao | Enantioselective Transformations Promoted by Cooperative Functions of an Achiral Lewis Acid and a Chiral Lewis Acid | |
| CN115477667A (zh) | 一种手性含硅立体中心四取代硅烷化合物的制备方法 | |
| Moreau | Chiral nitrogen ligands in asymmetric catalysis | |
| Bland et al. | Reaction of Alpine-Borane with Aldehydes: Reactivity Rate Assessment by Observation of the Disappearance of the Carbonyl n-Pi* Peak by UV-Visible Spectroscopy | |
| EP0708764A1 (en) | Enanthioselective preparation of thiazole derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |