Synthesis of mexiletine stereoisomers and related compounds via SNAr nucleophilic substitution of a Cr (CO) 3-complexed aromatic fluoride

DG Loughhead, LA Flippin…

Index: Loughhead, David G.; Flippin, Lee A.; Weikert, Robert J. Journal of Organic Chemistry, 1999 , vol. 64, # 9 p. 3373 - 3375

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Citation Number: 26

Abstract

As part of a program aimed at discovering new sodium channel blockers, we required authentic samples of the enantiomers of the class IB antiarrhythmic agent mexiletine (1). 1 Both enantiomers of mexiletine have previously been prepared via classical resolution2, 3 and via enzymatic hydrolysis of an N-acyl derivative. 4 Recently, the (R)-isomer of mexiletine was prepared in 7.2% overall yield using a stereospecific, four-step procedure which ...