Abstract
The enantioselectivity of the lipase-catalyzed acetylation of several ( RS)-2-(1-aminoethyl)-3-chloro-5-(substituted)pyridines has been examined. An enantiomeric excess (substrate) of 94% at 55% conversion was obtained for acetylation of the ( R)-isomer of ( RS)-2-(1-aminoethyl)-3-chloro-5-bromopyridine by Candida antartica lipase B in ethyl acetate, whereas the ( R)-isomer of ( RS)-2-(1-aminoethyl)-3,5-dichloropyridine and ( RS)-2-(1-aminoethyl)-3-chloro-5-(difluoromethoxy)pyridine were each acetylated with significantly lower enantioselectivity. Substitution of methyl propionate, methyl isobutyrate or methyl methoxyacetate for ethyl acetate resulted in decreased enantioselectivity.
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