EP1725674A1 - Verfahren zur herstellung von chiralen, sekundären alkoholen - Google Patents
Verfahren zur herstellung von chiralen, sekundären alkoholenInfo
- Publication number
- EP1725674A1 EP1725674A1 EP05707624A EP05707624A EP1725674A1 EP 1725674 A1 EP1725674 A1 EP 1725674A1 EP 05707624 A EP05707624 A EP 05707624A EP 05707624 A EP05707624 A EP 05707624A EP 1725674 A1 EP1725674 A1 EP 1725674A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- alcohol
- formula
- amino
- defined above
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
-
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Definitions
- the present invention relates to a process for the production of chiral, secondary alcohols in an optical purity of up to 100% ee and in up to 100% yield.
- S means a “spectator” ligand, a neutral ligand that is difficult to exchange, and from the group of olefins, dienes or aromatics, such as benzene, toluene, xylene, cumene, cymene, naphthalene, anisole, chlorobenzene, indole, cyclopentadiene - nyl derivatives, tetraphenyl, cyclopentadienone, dihydroindole, tetrahydronaphthalene, gallic acid, benzoic acid and phenylglycine, and L is a neutral ligand which is relatively easy to replace by another ligand and from the group of acetonitrile, DMSO, methanol, water, THF,
- the transition metal compound can also be converted into a transition metal complex in which the neutral ligand is exchanged with another ligand or by complexing the transition metal compound with a ligand.
- a base is added to activate the catalyst.
- the base can be selected from the group of alkali or alkaline earth carbonates or bicarbonates. Examples include sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, etc.
- the catalyst is used in an amount of 0.005 to 0.1 mol% based on ketone or racemic alcohol, preferably 0.01 to 0.03 mol%.
- C 2 -C 6 alkenyl esters of aliphatic Ci to C ⁇ carboxylic acids can be used as acyl donors, 1-propenyl, vinyl or isopropenyl propionate or butyrate are preferred.
- the entire amount of the acyl donor, which is used in an amount of 0.5 to 1.0 equivalents based on the ketone, can be charged or added slowly.
- a small amount of activated carbon and a filter aid are preferably added to the reaction mixture and stirred for some time.
- the mixture is filtered off, the filter cake is washed with solvent and the filtrate is diluted with solvent. It is cooled, inoculated and the product crystallizes at temperatures from -20 to 0 ° C.
- the (S) -alcohol of the general formula (I) thus obtained is washed with solvent and dried at room temperature under vacuum.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT0047104A AT500556A1 (de) | 2004-03-18 | 2004-03-18 | Verfahren zur herstellung von chiralen, sekundären alkoholen |
PCT/EP2005/001977 WO2005095628A1 (de) | 2004-03-18 | 2005-02-25 | Verfahren zur herstellung von chiralen, sekundären alkoholen |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1725674A1 true EP1725674A1 (de) | 2006-11-29 |
Family
ID=34960671
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05707624A Withdrawn EP1725674A1 (de) | 2004-03-18 | 2005-02-25 | Verfahren zur herstellung von chiralen, sekundären alkoholen |
Country Status (7)
Country | Link |
---|---|
US (1) | US20070196904A1 (zh) |
EP (1) | EP1725674A1 (zh) |
JP (1) | JP2007529207A (zh) |
CN (1) | CN1934267A (zh) |
AT (1) | AT500556A1 (zh) |
NO (1) | NO20064686L (zh) |
WO (1) | WO2005095628A1 (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102851349A (zh) * | 2012-09-27 | 2013-01-02 | 南京工业大学 | 同时获得两种单一手性仲醇的方法 |
CN105132394B (zh) * | 2015-09-24 | 2018-03-16 | 中国科学院南海海洋研究所 | 一种脂肪酶lipase6及其编码基因和应用 |
CN109735582B (zh) * | 2018-12-24 | 2022-06-21 | 浙江工业大学 | 一种脂肪酶催化在线合成环己醇类β-氨基醇衍生物的方法 |
CN110240538B (zh) * | 2019-06-27 | 2022-04-22 | 万华化学集团股份有限公司 | 一种制备高碳支链仲醇的方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3743824C2 (de) * | 1987-12-23 | 1997-03-06 | Hoechst Ag | Verfahren zur enzymatischen Racematspaltung von racemischen Alkoholen mit/in Vinylestern durch Umesterung |
JP3638643B2 (ja) * | 1994-10-14 | 2005-04-13 | 高砂香料工業株式会社 | 光学活性1−オクテン−3−オールの製造法 |
AU2002365968A1 (en) * | 2001-11-19 | 2003-06-10 | Merck And Co., Inc. | Process for the synthesis of (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol and esters thereof by dynamic kinetic resolution |
-
2004
- 2004-03-18 AT AT0047104A patent/AT500556A1/de not_active Application Discontinuation
-
2005
- 2005-02-25 WO PCT/EP2005/001977 patent/WO2005095628A1/de not_active Application Discontinuation
- 2005-02-25 US US10/592,758 patent/US20070196904A1/en not_active Abandoned
- 2005-02-25 CN CNA2005800085598A patent/CN1934267A/zh active Pending
- 2005-02-25 JP JP2007503220A patent/JP2007529207A/ja not_active Withdrawn
- 2005-02-25 EP EP05707624A patent/EP1725674A1/de not_active Withdrawn
-
2006
- 2006-10-17 NO NO20064686A patent/NO20064686L/no not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO2005095628A1 * |
Also Published As
Publication number | Publication date |
---|---|
CN1934267A (zh) | 2007-03-21 |
US20070196904A1 (en) | 2007-08-23 |
JP2007529207A (ja) | 2007-10-25 |
AT500556A1 (de) | 2006-01-15 |
NO20064686L (no) | 2006-12-18 |
WO2005095628A1 (de) | 2005-10-13 |
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Legal Events
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PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
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17P | Request for examination filed |
Effective date: 20060826 |
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AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR |
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DAX | Request for extension of the european patent (deleted) | ||
17Q | First examination report despatched |
Effective date: 20080411 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20081022 |