Synthesis of (R)-, (S)-, and (RS)-hydroxymethylmexiletine one of the major metabolites of mexiletine

Abstract

Hydroxymethylmexiletine (HMM), one of the main metabolites of mexiletine, has been synthesized in both racemic and optically active forms following two alternative routes. The ee values for both HMM enantiomers were 98%, as assessed by H-1 NMR analysis in the presence of (-)-(R)-(2-naphthyloxy) phenylacetic acid as a chiral solvating agent and electrophoretic analysis using beta-cyclodextrine sulfated sodium salt as a chiral auxiliary