title: Asymmetric synthesis of an antagonist of neurokinin receptors: SSR 241586.
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.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Thomas-Xavier
authors.initials: TX
authors.lastname: Métro
authors.forename: Anne
authors.initials: A
authors.lastname: Cochi
authors.forename: Domingo
authors.initials: D
authors.lastname: Gomez Pardo
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D000478:Alkylation; D000586:Amination; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D002384:Catalysis; D006801:Humans; D043183:Irritable Bowel Syndrome / Q000188:drug therapy; D009025:Morpholines / Q000138:chemical synthesis* / Q000627:therapeutic use; D018377:Neurotransmitter Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D010084:Oxidation-Reduction; D018039:Receptors, Tachykinin / Q000037:antagonists & inhibitors* / Q000378:metabolism; D012559:Schizophrenia / Q000188:drug therapy; D013237:Stereoisomerism
chemical_list: D000893:Anti-Inflammatory Agents; D009025:Morpholines; D018377:Neurotransmitter Agents; D018039:Receptors, Tachykinin; C553354:SSR 241586