Concise, Protecting-Group-Free Synthesis of (+)-Nemonapride via Eu(OTf)3-Catalyzed Aminolysis of 3,4-Epoxy Alcohol

Chem Pharm Bull (Tokyo). 2017;65(1):22-24. doi: 10.1248/cpb.c16-00568.

Abstract

A concise, protecting-group-free synthesis of the antipsychotic agent (+)-nemonapride has been achieved featuring a europium(III) trifluoromethanesulfonate (Eu(OTf)3)-catalyzed C4 selective aminolysis of a 3,4-epoxy alcohol by benzylamine and an expedient use of the resulting 4-benzylamino-1,3-diol product for constructing the pyrrolidine skeleton.

MeSH terms

  • Alcohols / chemistry*
  • Amines / chemistry*
  • Benzamides / chemical synthesis*
  • Benzamides / chemistry
  • Catalysis
  • Epoxy Compounds / chemistry*
  • Mesylates / chemistry*
  • Molecular Structure

Substances

  • 3,4-epoxy alcohol
  • Alcohols
  • Amines
  • Benzamides
  • Epoxy Compounds
  • Mesylates
  • trifluoromethanesulfonic acid
  • nemonapride