A convenient synthesis of enantiomerically pure (R)-mexiletine using hydrolytic kinetic resolution method

Enantiopure (R)-mexiletine was prepared in a simple and practical way using hydrolytic kinetic resolution method of terminal epoxide by Jacobsen’s catalyst. High enantiomeric purity (98% ee) was achieved and the method is well amenable to industrial scale-up.

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(S)-2-(2,6-Dimethylphenoxymethyl)oxiraneC11H14O2[α]D25=+2.5 (c 2, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (S)

(R)-3-(2,6-Dimethylphenoxy)propane-1,2-diolC11H16O3[α]D25=-3 (c 2, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (R)