Asymmetric synthesis of an antagonist of neurokinin receptors: SSR 241586

J Org Chem. 2011 Apr 15;76(8):2594-602. doi: 10.1021/jo102471r. Epub 2011 Mar 16.

Abstract

SSR 241586 is a 2,2-disubstituted morpholine, developed by Sanofi-Aventis, which is active in the treatment of schizophrenia and irritable bowel syndrome (IBS). Different strategies have been studied to synthesize this molecule and among the strategies an organo-catalyzed Henry reaction, applied to an α-keto ester, has produced SSR 241586 in excellent enantiomeric excess.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Amination
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / therapeutic use
  • Catalysis
  • Humans
  • Irritable Bowel Syndrome / drug therapy
  • Morpholines / chemical synthesis*
  • Morpholines / therapeutic use
  • Neurotransmitter Agents / chemical synthesis*
  • Neurotransmitter Agents / therapeutic use
  • Oxidation-Reduction
  • Receptors, Tachykinin / antagonists & inhibitors*
  • Receptors, Tachykinin / metabolism
  • Schizophrenia / drug therapy
  • Stereoisomerism

Substances

  • Anti-Inflammatory Agents
  • Morpholines
  • Neurotransmitter Agents
  • Receptors, Tachykinin
  • SSR 241586