A simple, scalable synthetic route to (+)- and (-)-pseudoephenamine

Org Lett. 2013 Nov 1;15(21):5594-7. doi: 10.1021/ol402815d. Epub 2013 Oct 18.

Abstract

A three-step synthesis of pseudoephenamine suitable for preparing multigram amounts of both enantiomers of the auxiliary from the inexpensive starting material benzil is described. The sequence involves synthesis of the crystalline monomethylimine derivative of benzil, reduction of that substance with lithium aluminum hydride, and resolution of pseudoephenamine with mandelic acid.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amphetamine / chemical synthesis*
  • Amphetamine / chemistry
  • Amphetamines / chemical synthesis*
  • Amphetamines / chemistry
  • Benzyl Compounds / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amphetamines
  • Benzyl Compounds
  • pseudoephenamine
  • Amphetamine