Preparation of 1-Pyridinylethanols of High Enantiomeric Purity by Lipase Catalysed Transesterifications

Article abstract of DOI:10.1016/0957-4166(94)80178-9

Component B lipase of the Candida antarctica yeast displays high enantioselectivity in catalysing transesterification reactions in non-aqueous media with chiral secondary alcohols.This was exploited to resolve racemates of 1-(pyridinyl)-ethanols, 1-(6-bromopyridin-2-yl)ethanol, and 1-(6-bromopyridin-2-yl)-2,2-dimethylpropanol.The lipase esterified the (R)-alcohols of the first four substrates in equal or more than 99percent enantiomeric excess in less than three hours with 30-40percent isolated yield.Remaining (S)-enantiomers were isolated in similar yields and in 97-98percent ee. 1-(6-Bromopyridin-2-yl)-2,2-dimethylpropanol did not form any detectable ester in one week.