JP2011518150A - イミンの水素化 - Google Patents
イミンの水素化 Download PDFInfo
- Publication number
- JP2011518150A JP2011518150A JP2011504607A JP2011504607A JP2011518150A JP 2011518150 A JP2011518150 A JP 2011518150A JP 2011504607 A JP2011504607 A JP 2011504607A JP 2011504607 A JP2011504607 A JP 2011504607A JP 2011518150 A JP2011518150 A JP 2011518150A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- imine
- diphenylphosphino
- bis
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002466 imines Chemical class 0.000 title claims abstract description 62
- 238000005984 hydrogenation reaction Methods 0.000 title abstract description 39
- 239000003054 catalyst Substances 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 67
- 230000008569 process Effects 0.000 claims abstract description 44
- 150000001412 amines Chemical class 0.000 claims abstract description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 claims abstract description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 70
- 239000003446 ligand Substances 0.000 claims description 62
- -1 3,5-dimethylphenyl Chemical group 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 239000000654 additive Substances 0.000 claims description 26
- 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 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 230000000996 additive effect Effects 0.000 claims description 15
- 229910052741 iridium Inorganic materials 0.000 claims description 14
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 12
- 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 description 12
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000010948 rhodium Substances 0.000 claims description 11
- 229910052703 rhodium Inorganic materials 0.000 claims description 8
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 6
- ZBCKWHYWPLHBOK-UHFFFAOYSA-N cyclohexylphosphane Chemical compound PC1CCCCC1 ZBCKWHYWPLHBOK-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 239000012454 non-polar solvent Substances 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 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 description 2
- 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 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 claims description 2
- 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 description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 14
- 239000004009 herbicide Substances 0.000 abstract description 10
- 150000004658 ketimines Chemical class 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 67
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 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 13
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 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 6
- 239000005617 S-Metolachlor Substances 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 6
- 239000012467 final product Substances 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 230000007306 turnover Effects 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000012552 review Methods 0.000 description 4
- VURFVHCLMJOLKN-UHFFFAOYSA-N Diphosphine Natural products PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000002638 heterogeneous catalyst Substances 0.000 description 3
- 239000002815 homogeneous catalyst Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YXWIRQHVEQIJOV-LLVKDONJSA-N CCc1cccc(C)c1N[C@H](C)COC Chemical compound CCc1cccc(C)c1N[C@H](C)COC YXWIRQHVEQIJOV-LLVKDONJSA-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
- 239000012018 catalyst precursor Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 210000003027 ear inner Anatomy 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011982 enantioselective catalyst Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- HIZBWIXMAQEVLW-UHFFFAOYSA-N 2,3,4-trimethylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C(C)=C(C)C1(C)C2 HIZBWIXMAQEVLW-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-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
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZLABTBYFTTTZJD-KAMYIIQDSA-N CC/C(/C)=N\c1c(CC)cccc1C Chemical compound CC/C(/C)=N\c1c(CC)cccc1C ZLABTBYFTTTZJD-KAMYIIQDSA-N 0.000 description 1
- KMDVAIKDILDJSS-PTNGSMBKSA-N CCC1=CCC(C)C(C)=C1/N=C(/C)\COC Chemical compound CCC1=CCC(C)C(C)=C1/N=C(/C)\COC KMDVAIKDILDJSS-PTNGSMBKSA-N 0.000 description 1
- WVQBLGZPHOPPFO-GFCCVEGCSA-N CCc1cccc(C)c1N([C@H](C)COC)C(CCl)=O Chemical compound CCc1cccc(C)c1N([C@H](C)COC)C(CCl)=O WVQBLGZPHOPPFO-GFCCVEGCSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 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
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004296 chiral HPLC 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 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 |
|---|---|
| JP2011518150A true JP2011518150A (ja) | 2011-06-23 |
| JP2011518150A5 JP2011518150A5 (enExample) | 2012-01-12 |
Family
ID=41265115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011504607A Pending JP2011518150A (ja) | 2008-04-17 | 2009-04-16 | イミンの水素化 |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019089766A (ja) * | 2013-03-11 | 2019-06-13 | ラトガース，ザ ステート ユニバーシティ オブ ニュー ジャージー | 不斉転換のための有機金属の触媒作用 |
Families Citing this family (10)
| 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 |
| 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 |
| CN109096137A (zh) * | 2018-07-30 | 2018-12-28 | 山东万豪肥业有限公司 | 一种精异丙甲草胺的合成方法 |
| 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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5312818A (en) * | 1972-06-06 | 1978-02-04 | Ciba Geigy Ag | Preparation of substituted chloroacetoanilide |
| JPS6357558A (ja) * | 1986-08-04 | 1988-03-12 | チバ・ガイギ−・アクチェンゲゼルシャフト | 光学活性な第二アリ−ルアミンの製造方法 |
| JPH08508753A (ja) * | 1994-02-02 | 1996-09-17 | チバ−ガイギー アクチエンゲゼルシャフト | イミンの水素化法 |
| JP2005531587A (ja) * | 2002-05-27 | 2005-10-20 | デグサ アクチエンゲゼルシャフト | ヒドロキシホスフィンおよびその触媒における使用 |
| JP2007537171A (ja) * | 2004-05-11 | 2007-12-20 | デグサ ゲーエムベーハー | シクロオレフィンホスフィン配位子及びその触媒中での使用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY109091A (en) * | 1992-12-29 | 1996-11-30 | Syngenta Participations Ag | Process for the preparation of 2-alkyl-6-methyl-n-(1''''''''- methoxy-2''''''''-propyl)-aniline and a process for the preparation of their chloracetanilides. |
| FR2750423B1 (fr) | 1996-06-28 | 1998-08-14 | Rhone Poulenc Chimie | Procede d'hydrogenation asymetrique d'un compose cetonique |
| 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 |
| US20070213540A1 (en) | 2006-03-09 | 2007-09-13 | Degussa Ag | Process for the hydrogenation of imines |
-
2009
- 2009-04-16 BR BRPI0907343A patent/BRPI0907343A8/pt not_active IP Right Cessation
- 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
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5312818A (en) * | 1972-06-06 | 1978-02-04 | Ciba Geigy Ag | Preparation of substituted chloroacetoanilide |
| JPS6357558A (ja) * | 1986-08-04 | 1988-03-12 | チバ・ガイギ−・アクチェンゲゼルシャフト | 光学活性な第二アリ−ルアミンの製造方法 |
| JPH08508753A (ja) * | 1994-02-02 | 1996-09-17 | チバ−ガイギー アクチエンゲゼルシャフト | イミンの水素化法 |
| JP2005531587A (ja) * | 2002-05-27 | 2005-10-20 | デグサ アクチエンゲゼルシャフト | ヒドロキシホスフィンおよびその触媒における使用 |
| JP2007537171A (ja) * | 2004-05-11 | 2007-12-20 | デグサ ゲーエムベーハー | シクロオレフィンホスフィン配位子及びその触媒中での使用 |
Non-Patent Citations (1)
| Title |
|---|
| JPN5009010275; ＴＡＮＧ Ｗ: ＣＨＥＭＩＣＡＬ ＲＥＶＩＥＷＳ Ｖ１０３ Ｎ８, 2003, Ｐ３０２９-３０６９, ＡＣＳ * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019089766A (ja) * | 2013-03-11 | 2019-06-13 | ラトガース，ザ ステート ユニバーシティ オブ ニュー ジャージー | 不斉転換のための有機金属の触媒作用 |
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 |
| RU2476422C2 (ru) | 2013-02-27 |
| RU2010145490A (ru) | 2012-05-27 |
| 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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