The lipase-catalyzed remote kinetic resolution of 4-[4-(dimethylamino)-1-(4-fluorophenyl)- 1-hydroxy-1-butyl]-3-(hydroxymethyl)-benzonitrile (1), a useful intermediate of citalopram with a quater-nary chiral center, was studied. Through screening, the preferable system for the asymmetric reaction was: Candida antarctica lipase B (Novozym435) as a catalyst, acetonitrile as a solvent and vinyl acetate as an acyl donor. The influence of various parameters on the enzymatic resolution was studied. The optimal con-dition was as follows: temperature of 30 ℃, the molar ratio of diol 1 to vinyl acetate 1 to 5, 10 mg/mL li-pase, and 200 r/min rotation speed. Reaction curves of 180 and 60 mmol/L diol 1 concentrations ensured the high reaction rate and enantioselectivity. Reusability study ensured the operational stability of lipase over repeated cycles.

Key words: lipase, organic media, remote kinetics resolution, citalopram, transesterification