EA033451B1 - Способ асимметрической гидрогенизации кеталей и ацеталей - Google Patents
Способ асимметрической гидрогенизации кеталей и ацеталейInfo
- Publication number
- EA033451B1 EA033451B1 EA201500667A EA201500667A EA033451B1 EA 033451 B1 EA033451 B1 EA 033451B1 EA 201500667 A EA201500667 A EA 201500667A EA 201500667 A EA201500667 A EA 201500667A EA 033451 B1 EA033451 B1 EA 033451B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- ketals
- acetals
- asymmetric hydrogenation
- iii
- formula
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B35/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving a change in the type of bonding between two carbon atoms already directly linked
- C07B35/02—Reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/189—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/58—Separation; Purification; Stabilisation; Use of additives
-
- 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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/827—Iridium
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- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Изобретение касается способа асимметрической гидрогенизации кеталей ненасыщенных кетонов или ацеталей ненасыщенных альдегидов молекулярным водородом в присутствии по меньшей мере одного хирального комплекса иридия формулы (III), где группы и символы в формуле (III) имеют значения, которые определены в настоящем описании. Этот способ дает хиральные соединения очень эффективным образом и очень выгоден тем, что можно значительно уменьшить количество комплекса иридия.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12197861 | 2012-12-18 | ||
PCT/EP2013/077231 WO2014096096A1 (en) | 2012-12-18 | 2013-12-18 | Process of asymmetric hydrogenation of ketals and acetals |
Publications (2)
Publication Number | Publication Date |
---|---|
EA201500667A1 EA201500667A1 (ru) | 2015-12-30 |
EA033451B1 true EA033451B1 (ru) | 2019-10-31 |
Family
ID=47500978
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EA201500667A EA033451B1 (ru) | 2012-12-18 | 2013-12-18 | Способ асимметрической гидрогенизации кеталей и ацеталей |
Country Status (8)
Country | Link |
---|---|
US (1) | US9561989B2 (ru) |
EP (1) | EP2935233B1 (ru) |
JP (1) | JP6476496B2 (ru) |
CN (1) | CN104884446A (ru) |
BR (1) | BR112015014284B1 (ru) |
EA (1) | EA033451B1 (ru) |
MY (1) | MY170541A (ru) |
WO (1) | WO2014096096A1 (ru) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9458076B2 (en) * | 2012-12-18 | 2016-10-04 | Dsm Ip Assets B.V. | Using mixtures of E/Z isomers to obtain quantitatively specific products by combined asymmetric hydrogenations |
GB201717210D0 (en) | 2017-10-19 | 2017-12-06 | Bp Plc | Selective acetalization/etherification process |
GB201717211D0 (en) | 2017-10-19 | 2017-12-06 | Bp Plc | Etherification process |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0565975A2 (de) * | 1992-04-16 | 1993-10-20 | F. Hoffmann-La Roche Ag | Verfahren zur Herstellung von Isoprenderivaten |
WO2006066863A1 (en) * | 2004-12-22 | 2006-06-29 | Dsm Ip Assets B.V. | Asymmetric hydrogenation of alkennes using chiral iridium complexes |
EP2275398A1 (en) * | 2008-04-25 | 2011-01-19 | Zhejiang Jiuzhou Pharmaceutical Co., Ltd. | Application of the iridium complex in asymmetric catalytic hydrogenation for unsaturated carboxylic acid |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE210655T1 (de) * | 1992-01-31 | 2001-12-15 | Hoffmann La Roche | Asymmetrische hydrierung |
US9573872B2 (en) * | 2012-12-18 | 2017-02-21 | Dsm Ip Assets B.V. | Using mixtures of E/Z isomers to obtain quantitatively specific products by combining asymmetric hydrogenation and isomerization |
BR112015014335B1 (pt) * | 2012-12-18 | 2020-12-08 | Dsm Ip Assets B.V. | (6r,10r)-6,10,14-trimetilpentadecan-2-ona preparada a partir de 6,10-dimetilundec-5-en-2-ona ou 6,10 dimetilundeca-5,9-dien-2-ona |
US9458076B2 (en) * | 2012-12-18 | 2016-10-04 | Dsm Ip Assets B.V. | Using mixtures of E/Z isomers to obtain quantitatively specific products by combined asymmetric hydrogenations |
-
2013
- 2013-12-18 US US14/652,562 patent/US9561989B2/en active Active
- 2013-12-18 MY MYPI2015701887A patent/MY170541A/en unknown
- 2013-12-18 EP EP13811497.0A patent/EP2935233B1/en active Active
- 2013-12-18 JP JP2015547084A patent/JP6476496B2/ja active Active
- 2013-12-18 EA EA201500667A patent/EA033451B1/ru not_active IP Right Cessation
- 2013-12-18 WO PCT/EP2013/077231 patent/WO2014096096A1/en active Application Filing
- 2013-12-18 CN CN201380065931.3A patent/CN104884446A/zh active Pending
- 2013-12-18 BR BR112015014284A patent/BR112015014284B1/pt active IP Right Grant
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0565975A2 (de) * | 1992-04-16 | 1993-10-20 | F. Hoffmann-La Roche Ag | Verfahren zur Herstellung von Isoprenderivaten |
WO2006066863A1 (en) * | 2004-12-22 | 2006-06-29 | Dsm Ip Assets B.V. | Asymmetric hydrogenation of alkennes using chiral iridium complexes |
EP2275398A1 (en) * | 2008-04-25 | 2011-01-19 | Zhejiang Jiuzhou Pharmaceutical Co., Ltd. | Application of the iridium complex in asymmetric catalytic hydrogenation for unsaturated carboxylic acid |
Non-Patent Citations (2)
Title |
---|
JIAN-HUA XIE, XIAO-YAN LIU, JIAN-BO XIE, LI-XIN WANG, QI-LIN ZHOU: "An Additional Coordination Group Leads to Extremely Efficient Chiral Iridium Catalysts for Asymmetric Hydrogenation of Ketones", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, �VERLAG CHEMIE| :, vol. 50, no. 32, 1 August 2011 (2011-08-01), pages 7329 - 7332, XP055060237, ISSN: 14337851, DOI: 10.1002/anie.201102710 * |
SMIDT S P, ET AL.: "ENANTIOSELECTIVE HYDROGENATION OF ALKENES WITH IRIDIUM-PHOX CATALYSTS: A KINETIC STUDY OF ANION EFFECTS", CHEMISTRY - A EUROPEAN JOURNAL, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 10, no. 19, 1 January 2004 (2004-01-01), DE, pages 4685 - 4693, XP008045587, ISSN: 0947-6539, DOI: 10.1002/chem.200400284 * |
Also Published As
Publication number | Publication date |
---|---|
EP2935233A1 (en) | 2015-10-28 |
WO2014096096A1 (en) | 2014-06-26 |
JP2016501269A (ja) | 2016-01-18 |
JP6476496B2 (ja) | 2019-03-06 |
BR112015014284A8 (pt) | 2019-10-08 |
BR112015014284A2 (pt) | 2017-07-11 |
EA201500667A1 (ru) | 2015-12-30 |
US20160185683A1 (en) | 2016-06-30 |
US9561989B2 (en) | 2017-02-07 |
MY170541A (en) | 2019-08-15 |
EP2935233B1 (en) | 2019-01-30 |
CN104884446A (zh) | 2015-09-02 |
BR112015014284B1 (pt) | 2020-01-21 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG TJ TM RU |