engleski

Preparation of novel meta and para substituted N- benzyl protected quinuclidine esters and their resolution with butyrylcholinesterase

Since the optically active quinuclidin-3-ol is an important intermediate in the preparation of physiologically or pharmacologically active compounds, new biocatalytic method for the production of chiral quinuclidin-3-ols was examined. Butyrylcholinesterase (BChE ; EC 3.1.1.8) was chosen as a biocatalyst in a preparative kinetic resolution of enantiomers. A series of racemic, (R)- and (S)- esters of quinuclidin-3-ol and acetic, benzoic, phthalic and isonicotinic acids were synthesized as well as their racemic and chiral, quaternary N-benzyl, meta and para N-bromobenzyl and meta and para N- methylbenzyl derivatives. After the resolution, all N-benzyl protected groups were successfully removed by catalytic transfer hydrogenation with ammonium formate (10% Pd-C).

quinuclidin-3-ol ; esters ; resolution ; butyrylcholinesterase ; N-benzyl protected groups

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