A Robust, Recyclable Resin for Decagram Scale Resolution of (±)-Mefloquine and Other Chiral N-Heterocycles

Angew Chem Int Ed Engl. 2016 Jan 22;55(4):1553-6. doi: 10.1002/anie.201509256. Epub 2015 Dec 11.

Abstract

Decagram quantities of enantiopure (+)-mefloquine have been produced via kinetic resolution of racemic mefloquine using a ROMP-gel supported chiral acyl hydroxamic acid resolving agent. The requisite monomer was prepared in a few synthetic steps without chromatography and polymerization was safely performed on a >30 gram scale under ambient conditions. The reagent was readily regenerated and reused multiple times for the resolution of 150 grams of (±)-mefloquine and other chiral N-heterocylces.

Keywords: N-heterocycles; amines; enantioselective acylation; kinetic resolution; polymerization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / chemistry*
  • Heterocyclic Compounds / chemistry*
  • Mefloquine / chemistry*
  • Stereoisomerism

Substances

  • Antimalarials
  • Heterocyclic Compounds
  • Mefloquine