RU2476422C2 - Гидрирование иминов - Google Patents
Гидрирование иминов Download PDFInfo
- Publication number
- RU2476422C2 RU2476422C2 RU2010145490/04A RU2010145490A RU2476422C2 RU 2476422 C2 RU2476422 C2 RU 2476422C2 RU 2010145490/04 A RU2010145490/04 A RU 2010145490/04A RU 2010145490 A RU2010145490 A RU 2010145490A RU 2476422 C2 RU2476422 C2 RU 2476422C2
- Authority
- RU
- Russia
- Prior art keywords
- diphenylphosphino
- formula
- imine
- ligand
- bis
- Prior art date
Links
- 150000002466 imines Chemical class 0.000 title claims abstract description 57
- 238000005984 hydrogenation reaction Methods 0.000 title description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 99
- 238000006243 chemical reaction Methods 0.000 claims abstract description 93
- 239000003446 ligand Substances 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 62
- 239000003054 catalyst Substances 0.000 claims abstract description 50
- 150000001412 amines Chemical class 0.000 claims abstract description 37
- 239000000654 additive Substances 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 27
- 230000000996 additive effect Effects 0.000 claims abstract description 24
- -1 diphenylphosphinomethyl Chemical group 0.000 claims abstract description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 claims abstract description 15
- 239000002184 metal Substances 0.000 claims abstract description 14
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- UEWNEQVNIYYFFF-UHFFFAOYSA-N triphenylphosphanium;dibromide Chemical compound [Br-].[Br-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 UEWNEQVNIYYFFF-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 11
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000010948 rhodium Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 6
- QSOXMQSDXWBSSU-BPLGVMTJSA-N [(1S,12S,15R)-1-(diphenylphosphanylmethyl)-15-methyl-3,10-diazatetracyclo[10.2.1.02,11.04,9]pentadeca-2,4,6,8,10-pentaen-15-yl]methyl-diphenylphosphane Chemical compound C([C@@]12CC[C@](C3=NC4=CC=CC=C4N=C32)([C@@]1(C)CP(C=1C=CC=CC=1)C=1C=CC=CC=1)[H])P(C=1C=CC=CC=1)C1=CC=CC=C1 QSOXMQSDXWBSSU-BPLGVMTJSA-N 0.000 claims abstract description 5
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims abstract description 5
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 claims abstract description 3
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims abstract description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 3
- HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 claims abstract description 3
- KNHSKNWWDSSJKI-UHFFFAOYSA-N triphenylphosphanium diiodide Chemical compound [I-].[I-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 KNHSKNWWDSSJKI-UHFFFAOYSA-N 0.000 claims abstract description 3
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 claims abstract 2
- FBXGIVCVOWMMNI-UHFFFAOYSA-L trifluoromethanesulfonate;ytterbium(2+) Chemical compound [Yb+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F FBXGIVCVOWMMNI-UHFFFAOYSA-L 0.000 claims abstract 2
- HZKJMTZOHOPCOR-WEQWWUEYSA-N [(1r,2r,3s)-2,3-bis(diphenylphosphanylmethyl)-1,2-dimethylcyclopentyl]methanol Chemical compound C([C@H]1CC[C@]([C@]1(C)CP(C=1C=CC=CC=1)C=1C=CC=CC=1)(CO)C)P(C=1C=CC=CC=1)C1=CC=CC=C1 HZKJMTZOHOPCOR-WEQWWUEYSA-N 0.000 claims description 26
- 230000003197 catalytic effect Effects 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 claims description 4
- DPOGTJDEMBEUSH-UHFFFAOYSA-N dicyclohexyl(ethyl)phosphane Chemical compound C1CCCCC1P(CC)C1CCCCC1 DPOGTJDEMBEUSH-UHFFFAOYSA-N 0.000 claims description 4
- 239000012454 non-polar solvent Substances 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 230000000536 complexating effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 10
- 230000002363 herbicidal effect Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 238000005260 corrosion Methods 0.000 abstract description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract description 2
- WIOADUFWOUUQCV-UHFFFAOYSA-N triphenylphosphanium dichloride Chemical compound [Cl-].[Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 WIOADUFWOUUQCV-UHFFFAOYSA-N 0.000 abstract description 2
- 229940126214 compound 3 Drugs 0.000 abstract 2
- CMEPUAROFJSGJN-UHFFFAOYSA-N 1,4-dioxan-2-ylmethanol Chemical compound OCC1COCCO1 CMEPUAROFJSGJN-UHFFFAOYSA-N 0.000 abstract 1
- FOBHBDUEDTWUIL-UHFFFAOYSA-N benzylphosphane;hydrobromide Chemical compound [Br-].[PH3+]CC1=CC=CC=C1 FOBHBDUEDTWUIL-UHFFFAOYSA-N 0.000 abstract 1
- NTEVYDVXXMVLIS-UHFFFAOYSA-N butylphosphane;hydroiodide Chemical compound [I-].CCCC[PH3+] NTEVYDVXXMVLIS-UHFFFAOYSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
- YRUUSCWNSWFUAF-UHFFFAOYSA-N n-(2-ethyl-6-methylphenyl)-1-methoxypropan-2-imine Chemical compound CCC1=CC=CC(C)=C1N=C(C)COC YRUUSCWNSWFUAF-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 20
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 description 8
- 239000005617 S-Metolachlor Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000002815 homogeneous catalyst Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- AEFPPQGZJFTXDR-UHFFFAOYSA-M tetraphenylphosphanium;iodide Chemical compound [I-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEFPPQGZJFTXDR-UHFFFAOYSA-M 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
- YXWIRQHVEQIJOV-NSHDSACASA-N 2-ethyl-n-[(2s)-1-methoxypropan-2-yl]-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N[C@@H](C)COC YXWIRQHVEQIJOV-NSHDSACASA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 0 CO[C@](C(CCCC1(*2CCCC2)[Te]C2(CCCCC2)C2(C3)C3CC2)C1P(c1ccccc1)c1ccccc1)c(cccc1)c1P(c1ccccc1)c1ccccc1 Chemical compound CO[C@](C(CCCC1(*2CCCC2)[Te]C2(CCCCC2)C2(C3)C3CC2)C1P(c1ccccc1)c1ccccc1)c(cccc1)c1P(c1ccccc1)c1ccccc1 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- YLQBEKUKMJWXMC-UHFFFAOYSA-N cyclopenta-1,3-diene cyclopenta-2,4-dien-1-ylphosphane iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.P[c-]1cccc1 YLQBEKUKMJWXMC-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000011982 enantioselective catalyst Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007866 imination reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001509 metal bromide Inorganic materials 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- BHAROVLESINHSM-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1 BHAROVLESINHSM-UHFFFAOYSA-N 0.000 description 1
- CILQKUOYIAVYFK-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1.CC1=CC=CC=C1.CC1=CC=CC=C1 CILQKUOYIAVYFK-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN877/MUM/2008 | 2008-04-17 | ||
| IN877MU2008 | 2008-04-17 | ||
| PCT/IN2009/000237 WO2009136409A2 (en) | 2008-04-17 | 2009-04-16 | Hydrogenation of imines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010145490A RU2010145490A (ru) | 2012-05-27 |
| RU2476422C2 true RU2476422C2 (ru) | 2013-02-27 |
Family
ID=41265115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010145490/04A RU2476422C2 (ru) | 2008-04-17 | 2009-04-16 | Гидрирование иминов |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8461386B2 (enExample) |
| EP (1) | EP2265373A4 (enExample) |
| JP (1) | JP2011518150A (enExample) |
| KR (1) | KR101245065B1 (enExample) |
| CN (1) | CN102006930B (enExample) |
| AU (1) | AU2009245307B2 (enExample) |
| BR (1) | BRPI0907343A8 (enExample) |
| RU (1) | RU2476422C2 (enExample) |
| UA (1) | UA100732C2 (enExample) |
| WO (1) | WO2009136409A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103189341B (zh) * | 2010-11-02 | 2015-06-17 | Upl有限公司 | 用于制备羟基膦配位体的手性中间体 |
| EP2892877B1 (en) * | 2012-09-06 | 2017-06-21 | Council of Scientific and Industrial Research | Process for the preparation of (s)-2-ethyl-n-(1-methoxypropan -2-yl)-6-methyl aniline |
| WO2014164801A1 (en) * | 2013-03-11 | 2014-10-09 | Rutgers, The State University Of New Jersey | Metallorganocatalysis for asymmetric transformations |
| CN104445068B (zh) * | 2014-11-21 | 2016-09-28 | 山东侨昌化学有限公司 | 一种异丙甲草胺生产过程中副产氢气的回收方法 |
| CN108218726B (zh) * | 2016-12-14 | 2020-08-18 | 浙江省化工研究院有限公司 | 一种制备(s)-mea胺醚的方法 |
| CN110551034B (zh) * | 2018-05-31 | 2021-11-09 | 中国科学院大连化学物理研究所 | 一种酮的不对称还原胺化方法 |
| CN110551037B (zh) * | 2018-05-31 | 2021-11-09 | 中国科学院大连化学物理研究所 | 一种铱/手性双膦体系催化亚胺不对称氢化方法 |
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| EP4003957B1 (en) * | 2019-07-25 | 2024-04-17 | Medichem, S.A. | Process for the synthesis of n-alkyl-4-pyridinamines |
| GB202216812D0 (en) * | 2022-11-10 | 2022-12-28 | Univ Court Univ St Andrews | Process |
| CN120699067B (zh) * | 2025-08-18 | 2025-11-21 | 瑞博(苏州)制药有限公司 | 新型手性二茂铁桥联联萘骨架膦配体及其应用 |
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| EP1206427B1 (en) * | 1999-08-23 | 2005-11-09 | The Penn State Research Foundation | Chiral ligands, transition-metal complexes thereof and uses thereof in asymmetric reactions |
| DE10223593A1 (de) * | 2002-05-27 | 2003-12-11 | Degussa | Hydroxydiphosphine und deren Verwendung in der Katalyse |
| EP1595888A1 (en) * | 2004-05-11 | 2005-11-16 | Degussa AG | Cycloolefin phosphine ligands and their use in catalysis |
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- 2009-04-16 CN CN2009801129731A patent/CN102006930B/zh not_active Expired - Fee Related
- 2009-04-16 RU RU2010145490/04A patent/RU2476422C2/ru not_active IP Right Cessation
- 2009-04-16 EP EP09742576.3A patent/EP2265373A4/en not_active Withdrawn
- 2009-04-16 UA UAA201013378A patent/UA100732C2/ru unknown
- 2009-04-16 WO PCT/IN2009/000237 patent/WO2009136409A2/en not_active Ceased
- 2009-04-16 US US12/935,166 patent/US8461386B2/en active Active
- 2009-04-16 AU AU2009245307A patent/AU2009245307B2/en not_active Ceased
- 2009-04-16 KR KR1020107019544A patent/KR101245065B1/ko not_active Expired - Fee Related
- 2009-04-16 JP JP2011504607A patent/JP2011518150A/ja active Pending
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20100133370A (ko) | 2010-12-21 |
| US20110054217A1 (en) | 2011-03-03 |
| AU2009245307B2 (en) | 2014-01-30 |
| EP2265373A4 (en) | 2014-04-23 |
| BRPI0907343A2 (pt) | 2015-07-28 |
| WO2009136409A3 (en) | 2009-12-30 |
| RU2010145490A (ru) | 2012-05-27 |
| JP2011518150A (ja) | 2011-06-23 |
| BRPI0907343A8 (pt) | 2017-05-23 |
| KR101245065B1 (ko) | 2013-03-18 |
| EP2265373A2 (en) | 2010-12-29 |
| CN102006930B (zh) | 2013-09-25 |
| US8461386B2 (en) | 2013-06-11 |
| UA100732C2 (ru) | 2013-01-25 |
| WO2009136409A2 (en) | 2009-11-12 |
| AU2009245307A1 (en) | 2009-11-12 |
| CN102006930A (zh) | 2011-04-06 |
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