Convenient diastereospecific synthesis of a rociverine precursor and its resolution by lipase-catalyzed transesterification

Article abstract of DOI:10.1016/S0957-4166(96)00467-3

(±)-1-Cyclohexyl-c-2-hydroxymethyl-r-1-cyclohexanol 3, a precursor of the antimuscarinic drug Rociverine 1, was obtained diastereospecifically in very high yield, from the Grignard reaction between C₆H₁₁MgCl and an appropriately protected 2-hydroxymethyl)cyclohexanone. The preparation of enantiomerically enriched cis diol (+)-(1R, 2S-)-3 and the corresponding 2-acetoxymethyl derivative (+)-(1S,2R)-12 was achieved by lipase PPL-catalyzed transesterification of racemic diol (±)-3.