Abstract
Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the ( S)-alcohol and ( R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase ( Burkholderia cepacia) immobilized on modified ceramic particles (PS-C) in diisopropyl ether gave the best results. The use of base additives in this transesterification drastically reduces the reaction time without effecting the yields or enantioselectivities. Resolved 3-hydroxy-4-trityloxybutanenitrile has been utilized for the synthesis of enantiomerically pure 5-tosyloxymethyl-1,3-oxazolidine-2-one, which is an important intermediate for the preparation of β-adrenergic blocking agents and oxazolidinone based antimicrobial agents. Enantiomerically pure ( R)-3-hydroxy-4-trityloxybutanenitrile and ( S)-5-tosyloxymethyl-1,3-oxazolidine-2-one have been utilized in the enantioconvergent synthesis of ( R)-GABOB.
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