ES2567408T3 - Un proceso de hidrogenación de cetoésteres - Google Patents
Un proceso de hidrogenación de cetoésteres Download PDFInfo
- Publication number
- ES2567408T3 ES2567408T3 ES11730183.8T ES11730183T ES2567408T3 ES 2567408 T3 ES2567408 T3 ES 2567408T3 ES 11730183 T ES11730183 T ES 11730183T ES 2567408 T3 ES2567408 T3 ES 2567408T3
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- Prior art keywords
- solvent
- cimeno
- reaction
- binap
- catalyst
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- 238000005984 hydrogenation reaction Methods 0.000 title description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 115
- 239000002904 solvent Substances 0.000 claims abstract description 83
- 238000000034 method Methods 0.000 claims abstract description 80
- 239000003054 catalyst Substances 0.000 claims abstract description 78
- 238000006243 chemical reaction Methods 0.000 claims abstract description 65
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
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- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 7
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
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- 125000001033 ether group Chemical group 0.000 claims abstract description 5
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- 125000003118 aryl group Chemical group 0.000 claims description 15
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
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- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 claims 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 abstract description 3
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- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US333462P | 2001-11-27 | ||
| US33346210P | 2010-05-11 | 2010-05-11 | |
| EP10004966A EP2386536A1 (en) | 2010-05-11 | 2010-05-11 | A process for the hydrogenation of ketoesters |
| EP10004966 | 2010-05-11 | ||
| PCT/EP2011/002323 WO2011141160A1 (en) | 2010-05-11 | 2011-05-10 | A process for the hydrogenation of ketoesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2567408T3 true ES2567408T3 (es) | 2016-04-22 |
Family
ID=42246339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11730183.8T Active ES2567408T3 (es) | 2010-05-11 | 2011-05-10 | Un proceso de hidrogenación de cetoésteres |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8431741B2 (enExample) |
| EP (2) | EP2386536A1 (enExample) |
| JP (1) | JP6018046B2 (enExample) |
| KR (1) | KR101848763B1 (enExample) |
| CN (1) | CN102844293B (enExample) |
| ES (1) | ES2567408T3 (enExample) |
| TW (1) | TWI519505B (enExample) |
| WO (1) | WO2011141160A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102633664B (zh) * | 2012-03-30 | 2014-05-28 | 广西新晶科技有限公司 | 一种左旋肉碱的制备方法 |
| CN102633705A (zh) * | 2012-03-31 | 2012-08-15 | 石家庄利康医药科技有限公司 | 一种制备奥拉西坦的方法 |
| CN103709058B (zh) * | 2013-12-10 | 2015-09-02 | 苏州汉酶生物技术有限公司 | 一种左旋肉碱的合成方法 |
| CN105218371A (zh) * | 2015-09-24 | 2016-01-06 | 上海交通大学 | 光学纯的3-羟基-4-(2,4,5-三氟苯基)丁酸乙酯的制备方法 |
| CN109851506B (zh) * | 2019-01-30 | 2020-09-15 | 凯特立斯（深圳）科技有限公司 | 钌-双膦催化剂催化的简单酮的不对称还原胺化制备手性伯胺 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0699367B2 (ja) | 1987-06-11 | 1994-12-07 | 高砂香料工業株式会社 | 光学活性アルコ−ルの製法 |
| JPH0678277B2 (ja) | 1988-02-19 | 1994-10-05 | 高砂香料工業株式会社 | 光学活性アルコールおよびその誘導体の製造方法 |
| JPH0757758B2 (ja) | 1988-10-24 | 1995-06-21 | 高砂香料工業株式会社 | ルテニウム―ホスフィン錯体 |
| GB8911732D0 (en) | 1989-05-22 | 1989-07-05 | Ethyl Petroleum Additives Ltd | Lubricant compositions |
| IT1303757B1 (it) | 1998-11-16 | 2001-02-23 | Sigma Tau Ind Farmaceuti | Processo industriale per la produzione di l-carnitina. |
| NL1014280C2 (nl) * | 2000-02-03 | 2001-08-06 | Dsm Nv | Werkwijze voor de bereiding van melamine uit ureum. |
| JP4601779B2 (ja) * | 2000-07-25 | 2010-12-22 | 高砂香料工業株式会社 | 光学活性アルコールの製造方法 |
| GB0211716D0 (en) | 2002-05-22 | 2002-07-03 | Phoenix Chemicals Ltd | Process |
| GB2401864B (en) * | 2003-05-21 | 2007-11-14 | Phoenix Chemicals Ltd | Process and catalytic composition |
| EP1528053A1 (en) | 2003-10-31 | 2005-05-04 | Lonza Ag | Process for the preparation of (S)- or (R)-4-halo-3-hydroxybutyrates |
| US6939981B1 (en) * | 2004-06-25 | 2005-09-06 | Eastman Chemical Company | Ruthenium complexes of phosphine-aminophosphine ligands |
| JP2006206570A (ja) * | 2004-12-27 | 2006-08-10 | Nippon Synthetic Chem Ind Co Ltd:The | 光学活性β−ヒドロキシアミノ酸誘導体の製造方法 |
| CN101117304B (zh) * | 2006-08-03 | 2011-12-21 | 中国科学院化学研究所 | 一种进行不对称催化氢化反应的方法 |
| GB0822064D0 (en) * | 2008-12-03 | 2009-01-07 | Johnson Matthey Plc | Process for preparing cationic ruthenium complexes |
-
2010
- 2010-05-11 EP EP10004966A patent/EP2386536A1/en not_active Ceased
-
2011
- 2011-05-10 TW TW100116238A patent/TWI519505B/zh not_active IP Right Cessation
- 2011-05-10 US US13/104,114 patent/US8431741B2/en active Active
- 2011-05-10 EP EP11730183.8A patent/EP2569275B1/en active Active
- 2011-05-10 CN CN201180019495.7A patent/CN102844293B/zh active Active
- 2011-05-10 KR KR1020127029535A patent/KR101848763B1/ko active Active
- 2011-05-10 JP JP2013509468A patent/JP6018046B2/ja active Active
- 2011-05-10 WO PCT/EP2011/002323 patent/WO2011141160A1/en not_active Ceased
- 2011-05-10 ES ES11730183.8T patent/ES2567408T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| KR101848763B1 (ko) | 2018-05-28 |
| TWI519505B (zh) | 2016-02-01 |
| KR20130079394A (ko) | 2013-07-10 |
| EP2569275A1 (en) | 2013-03-20 |
| JP6018046B2 (ja) | 2016-11-02 |
| CN102844293A (zh) | 2012-12-26 |
| WO2011141160A1 (en) | 2011-11-17 |
| US8431741B2 (en) | 2013-04-30 |
| JP2013526493A (ja) | 2013-06-24 |
| EP2386536A1 (en) | 2011-11-16 |
| US20120016153A1 (en) | 2012-01-19 |
| TW201213280A (en) | 2012-04-01 |
| HK1179943A1 (zh) | 2013-10-11 |
| CN102844293B (zh) | 2016-01-27 |
| EP2569275B1 (en) | 2016-01-27 |
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