Title:
CONCISE PROCESS FOR PREPARING 3-PYRROLIDINE CARBOXYLIC ACID DERIVATIVES
Document Type and Number:
WIPO Patent Application WO/2018/025295
Kind Code:
A1
Abstract:
The present invention relates to a process for preparing 3-pyrrolidine carboxylic acid derivatives, and particularly a simple process for preparing 5-substituted 3-pyrrolidine carboxylic acid derivatives. In addition, the present invention relates to a novel pyrrolidine carboxylic acid derivative, its manufacture, pharmaceutical compositions containing it and its use as a catalyst.
Inventors:
TANAKA FUJIE (JP)
YIN FENG (JP)
YIN FENG (JP)
Application Number:
PCT/JP2016/004377
Publication Date:
February 08, 2018
Filing Date:
September 28, 2016
Export Citation:
Assignee:
OKINAWA INST SCIENCE & TECH SCHOOL CORP (JP)
International Classes:
C07D207/16; A61K31/22; A61K31/40; C07C201/12; C07C205/51
Foreign References:
| US20070117986A1 | 2007-05-24 |
Other References:
YIN, F. ET AL.: "Synthesis of 3-Pyrrolidinecarboxylic Acids via Enantioselective Organocatalytic Michael Addition of Nitroalkanes to 4-Oxopent-2-Enoate Derivatives", THE 136TH ANNUAL MEETING OF THE PHARMACEUTICAL SOCIETY OF JAPAN, vol. 2, 5 March 2016 (2016-03-05), pages 148
MITCHELL, C. E. T. ET AL.: "A versatile organocatalyst for the asymmetric conjugate addition of nitroalkanes to enones", CHEM. COMMUN., vol. 42, 2005, pages 5346 - 5348, XP055460227
MITCHELL, C. E. T. ET AL.: "An efficient, asymmetric organocatalyst-mediated conjugate", ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, pages 2039 - 2049, XP055460230
JUARISTI, E. ET AL.: "Asymmetric Synthesis of beta-Amino Acids. 1. Highly Diastereoselective Addition of a Racemic beta-Alanine Enolate Derivative to Electrophiles", J. ORG. CHEM., vol. 56, no. 7, 1991, pages 2553 - 2557, XP002327935
ZHANG, H. ET AL.: "Catalysis of 3-Pyrrolidinecarboxylic Acid and Related Pyrrolidine Derivatives in Enantioselective anti-Mannich-Type Reactions: Importance of the 3-Acid Group on Pyrrolidine for Stereocontrol", J. AM. CHEM. SOC., vol. 130, no. 3, 2008, pages 875 - 886, XP055460253
MITSUMORI, S. ET AL.: "Direct Asymmetric anti-Mannich-Type Reactions Catalyzed by a Designed Amino Acid", J. AM. CHEM. SOC., vol. 128, no. 4, 2006, pages 1040 - 1041, XP055050415
HALLAND, N. ET AL.: "Organocatalytic Asymmetric Conjugate Addition of Nitroalkanes to alpha,beta-Unsaturated Enones Using Novel Imidazoline Catalysts", J. ORG. CHEM., vol. 67, no. 24, 2002, pages 8331 - 8338, XP002233843
BALLINI, R. ET AL.: "Potassium Fluoride/Basic Alumina as Far Superior Heterogeneous Catalyst for the Chemoselective Conjugate Addition of Nitroalkanes to Electron-Poor Alkenes Having Two Electron-Withdrawing Groups in a- and beta-Positions", ADV. SYNTH. CATAL., vol. 348, no. 10+11, 2006, pages 1154 - 1156, XP055189361
DATABASE FILE REGISTRY retrieved from STN Database accession no. 1227911-60-5
WANG, Y. ET AL.: "An efficient enantioselective method for asymmetric Michael addition of nitroalkanes to a, beta-unsaturated aldehydes", CHEM. COMMUN., 2008, pages 1232 - 1234, XP055460258
LU , H.-H. ET AL.: "Highly enantioselective organocatalytic Michael addition of nitroalkanes to 4-oxo-enoates", CHEM. COMMUN., 2009, pages 4251 - 4253, XP055460259
MITCHELL, C. E. T. ET AL.: "A versatile organocatalyst for the asymmetric conjugate addition of nitroalkanes to enones", CHEM. COMMUN., vol. 42, 2005, pages 5346 - 5348, XP055460227
MITCHELL, C. E. T. ET AL.: "An efficient, asymmetric organocatalyst-mediated conjugate", ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, pages 2039 - 2049, XP055460230
JUARISTI, E. ET AL.: "Asymmetric Synthesis of beta-Amino Acids. 1. Highly Diastereoselective Addition of a Racemic beta-Alanine Enolate Derivative to Electrophiles", J. ORG. CHEM., vol. 56, no. 7, 1991, pages 2553 - 2557, XP002327935
ZHANG, H. ET AL.: "Catalysis of 3-Pyrrolidinecarboxylic Acid and Related Pyrrolidine Derivatives in Enantioselective anti-Mannich-Type Reactions: Importance of the 3-Acid Group on Pyrrolidine for Stereocontrol", J. AM. CHEM. SOC., vol. 130, no. 3, 2008, pages 875 - 886, XP055460253
MITSUMORI, S. ET AL.: "Direct Asymmetric anti-Mannich-Type Reactions Catalyzed by a Designed Amino Acid", J. AM. CHEM. SOC., vol. 128, no. 4, 2006, pages 1040 - 1041, XP055050415
HALLAND, N. ET AL.: "Organocatalytic Asymmetric Conjugate Addition of Nitroalkanes to alpha,beta-Unsaturated Enones Using Novel Imidazoline Catalysts", J. ORG. CHEM., vol. 67, no. 24, 2002, pages 8331 - 8338, XP002233843
BALLINI, R. ET AL.: "Potassium Fluoride/Basic Alumina as Far Superior Heterogeneous Catalyst for the Chemoselective Conjugate Addition of Nitroalkanes to Electron-Poor Alkenes Having Two Electron-Withdrawing Groups in a- and beta-Positions", ADV. SYNTH. CATAL., vol. 348, no. 10+11, 2006, pages 1154 - 1156, XP055189361
DATABASE FILE REGISTRY retrieved from STN Database accession no. 1227911-60-5
WANG, Y. ET AL.: "An efficient enantioselective method for asymmetric Michael addition of nitroalkanes to a, beta-unsaturated aldehydes", CHEM. COMMUN., 2008, pages 1232 - 1234, XP055460258
LU , H.-H. ET AL.: "Highly enantioselective organocatalytic Michael addition of nitroalkanes to 4-oxo-enoates", CHEM. COMMUN., 2009, pages 4251 - 4253, XP055460259
Attorney, Agent or Firm:
TSUKUNI & ASSOCIATES et al. (JP)
Download PDF: