Chemo-enzymatic synthesis of the antidepressant duloxetine and its enantiomer

Chirality. 2000 Jan;12(1):26-9. doi: 10.1002/(SICI)1520-636X(2000)12:1<26::AID-CHIR5>3.0.CO;2-Z.

Abstract

Sodium borohydride reduction of 3-chloro-1-(2-thienyl)-1-propanone gave the corresponding racemic alcohol which was kinetically resolved with lipase B from Candida antarctica as catalyst to yield the chiral building blocks (S)-3-chloro-1-(2-thienyl)-1-propanol and the corresponding (R)-butanoate. The enantiopure chiral building blocks were converted into Duloxetine and its enantiomer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antidepressive Agents / chemical synthesis*
  • Antidepressive Agents / isolation & purification
  • Candida / enzymology
  • Duloxetine Hydrochloride
  • Kinetics
  • Lipase / metabolism*
  • Saccharomyces cerevisiae / enzymology
  • Stereoisomerism
  • Thiophenes / chemical synthesis*
  • Thiophenes / isolation & purification

Substances

  • Antidepressive Agents
  • Thiophenes
  • Duloxetine Hydrochloride
  • Lipase