EA033451B1 - Способ асимметрической гидрогенизации кеталей и ацеталей - Google Patents

Способ асимметрической гидрогенизации кеталей и ацеталей

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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
Application number
EA201500667A
Other languages
English (en)
Other versions
EA201500667A1 (ru
Inventor
Werner Bonrath
Thomas Netscher
Jonathan Alan Medlock
Gerardus Karel Maria Verzijl
Vries Andreas Hendrikus Maria De
Original Assignee
Dsm Ip Assets Bv
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dsm Ip Assets Bv filed Critical Dsm Ip Assets Bv
Publication of EA201500667A1 publication Critical patent/EA201500667A1/ru
Publication of EA033451B1 publication Critical patent/EA033451B1/ru

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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
    • 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
    • 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

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  • 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.
EA201500667A 2012-12-18 2013-12-18 Способ асимметрической гидрогенизации кеталей и ацеталей EA033451B1 (ru)

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

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Family Applications (1)

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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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6390048B2 (ja) * 2012-12-18 2018-09-19 ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． 組み合わされた不斉水素化によって特定の生成物を定量的に得るためのｅ／ｚ異性体の混合物の使用
GB201717211D0 (en) 2017-10-19 2017-12-06 Bp Plc Etherification process
GB201717210D0 (en) 2017-10-19 2017-12-06 Bp Plc Selective acetalization/etherification process

Citations (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE210655T1 (de) * 1992-01-31 2001-12-15 Hoffmann La Roche Asymmetrische hydrierung
US9452961B2 (en) * 2012-12-18 2016-09-27 Dsm Ip Assets B.V. (6R,10R)-6,10,14-trimetylpentadecan-2-one prepared from 6,10-dimetylundec-5-en-2-one or 6,10-dimetylundeca-5,9-dien-2-one
JP6390048B2 (ja) * 2012-12-18 2018-09-19 ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． 組み合わされた不斉水素化によって特定の生成物を定量的に得るためのｅ／ｚ異性体の混合物の使用
BR112015014204B1 (pt) * 2012-12-18 2021-03-30 Dsm Ip Assets B.V. Processo de fabricação de compostos utilizando misturas de isômeros e/z para obter produtos quantitativamente específicos por combinação de hidrogenação assimétrica e isomerização

Patent Citations (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
BR112015014284A8 (pt) 2019-10-08
US9561989B2 (en) 2017-02-07
WO2014096096A1 (en) 2014-06-26
JP6476496B2 (ja) 2019-03-06
BR112015014284B1 (pt) 2020-01-21
MY170541A (en) 2019-08-15
CN104884446A (zh) 2015-09-02
JP2016501269A (ja) 2016-01-18
BR112015014284A2 (pt) 2017-07-11
EP2935233B1 (en) 2019-01-30
EA201500667A1 (ru) 2015-12-30
EP2935233A1 (en) 2015-10-28
US20160185683A1 (en) 2016-06-30

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