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EP2576553A4 - Highly selective asymmetric hydroformylation of (1s,4r) or (1r,4s)-2-azabicyclo[2.2.1]hept-5-en-3- one (+) or (-)-lactam - Google Patents

Highly selective asymmetric hydroformylation of (1s,4r) or (1r,4s)-2-azabicyclo[2.2.1]hept-5-en-3- one (+) or (-)-lactam

Info

Publication number
EP2576553A4
EP2576553A4 EP11787411.5A EP11787411A EP2576553A4 EP 2576553 A4 EP2576553 A4 EP 2576553A4 EP 11787411 A EP11787411 A EP 11787411A EP 2576553 A4 EP2576553 A4 EP 2576553A4
Authority
EP
European Patent Office
Prior art keywords
azabicyclo
hept
lactam
highly selective
asymmetric hydroformylation
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Withdrawn
Application number
EP11787411.5A
Other languages
German (de)
French (fr)
Other versions
EP2576553A2 (en
Inventor
Christopher James Cobley
Gary Noonan
Matthew Lee Clarke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dr Reddys Laboratories Ltd
Dr Reddys Laboratories Inc
Original Assignee
Dr Reddys Laboratories Ltd
Dr Reddys Laboratories Inc
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 Dr Reddys Laboratories Ltd, Dr Reddys Laboratories Inc filed Critical Dr Reddys Laboratories Ltd
Publication of EP2576553A2 publication Critical patent/EP2576553A2/en
Publication of EP2576553A4 publication Critical patent/EP2576553A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/36—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/08—Bridged systems
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Methods of producing the compounds of formula (22) and (23) or enantiomers thereof comprising hydroformylation of compounds of the formula (21) or their enantiomers: using Kelliphite as chiral ligand wherein R is -H or an amine-protecting group.
EP11787411.5A 2010-05-27 2011-05-26 Highly selective asymmetric hydroformylation of (1s,4r) or (1r,4s)-2-azabicyclo[2.2.1]hept-5-en-3- one (+) or (-)-lactam Withdrawn EP2576553A4 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US34889010P 2010-05-27 2010-05-27
PCT/US2011/038134 WO2011150205A2 (en) 2010-05-27 2011-05-26 Highly selective asymmetric hydroformylation of (1s,4r) or (1r,4s)-2-azabicyclo[2.2.1]hept-5-en-3- one (+) or (-)-lactam

Publications (2)

Publication Number Publication Date
EP2576553A2 EP2576553A2 (en) 2013-04-10
EP2576553A4 true EP2576553A4 (en) 2013-11-20

Family

ID=45004819

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11787411.5A Withdrawn EP2576553A4 (en) 2010-05-27 2011-05-26 Highly selective asymmetric hydroformylation of (1s,4r) or (1r,4s)-2-azabicyclo[2.2.1]hept-5-en-3- one (+) or (-)-lactam

Country Status (3)

Country Link
EP (1) EP2576553A4 (en)
IN (1) IN2012CN10271A (en)
WO (1) WO2011150205A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114716326B (en) * 2022-04-25 2024-01-05 岳阳昌德新材料有限公司 Process for producing diamine compound

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6166022A (en) * 1997-07-22 2000-12-26 Astrazeneca Uk Limited Compounds
US20070049587A1 (en) * 2005-09-01 2007-03-01 Zbinden Katrin G Factor Xa inhibitors

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6072844A (en) * 1983-09-29 1985-04-24 Mitsubishi Petrochem Co Ltd Method for producing polar functional group-containing formylnorbornane
CN1227466A (en) * 1996-06-14 1999-09-01 生物晶体药品股份有限公司 Substituted cyclopentane compounds useful as neuraminidase inhibitors
BR9813480A (en) 1997-12-17 2000-10-10 Biocryst Pharm Inc Substituted cyclopentane neuraminidase inhibitor compounds, composition and methods of inhibiting influenza virus neuraminidase and treatment of influenza virus infection

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6166022A (en) * 1997-07-22 2000-12-26 Astrazeneca Uk Limited Compounds
US20070049587A1 (en) * 2005-09-01 2007-03-01 Zbinden Katrin G Factor Xa inhibitors

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
BLANCO J M ET AL: "Divergent synthesis of two precursors of 3'-homo-2'-deoxy- and 2'-homo-3'-deoxy-carbocyclic nucleosides", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 58, no. 43, 21 October 2002 (2002-10-21), pages 8843 - 8849, XP004390194, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(02)01053-0 *
C.F. PALMER ET AL.: "Rearrangement of 2-azabicyclo[2.2.1]hept-5-en-3-ones. Synthesis of cis-3-aminocyclopentane carboxylic acid derivatives.", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANS 1, vol. 58, no. 8, 21 April 1992 (1992-04-21), pages 1021 - 1028, XP008165279, ISSN: 0300-922X *
GARY M. NOONAN ET AL: "Asymmetric Hydroformylation of an Enantiomerically Pure Bicyclic Lactam: Efficient Synthesis of Functionalised Cyclopentylamines", CHEMISTRY - A EUROPEAN JOURNAL, vol. 16, no. 43, 15 November 2010 (2010-11-15), pages 12788 - 12791, XP055083083, ISSN: 0947-6539, DOI: 10.1002/chem.201002233 *
HUANG J ET AL: "A highly enantioselective catalyst for asymmetric hydroformylation of [2.2.1]-bicyclic olefins", TETRAHEDRON LETTERS, PERGAMON, vol. 46, no. 45, 7 November 2005 (2005-11-07), pages 7831 - 7834, XP027862901, ISSN: 0040-4039, [retrieved on 20051107] *
See also references of WO2011150205A2 *

Also Published As

Publication number Publication date
EP2576553A2 (en) 2013-04-10
WO2011150205A3 (en) 2012-03-29
IN2012CN10271A (en) 2015-04-10
WO2011150205A2 (en) 2011-12-01

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