Racemic cyclohexyl(hydroxymethyl)cyclohexanol I (R = H), a precursor of the antimuscarinic drug Rociverine, was obtained diastereospecifically in very high yield, from the Grignard reaction between C6H11MgCl and an appropriately protected 2-(hydroxymethyl)cyclohexanone. The prepn. of enantiomerically enriched (+)-(1R,2S)-(hydroxymethyl)cyclohexanol II and the corresponding 2-acetoxymethyl deriv. (+)-(1S,2R)-I (R = Ac) was achieved by lipase PPL-catalyzed transesterification of racemic I (R = H) with vinyl acetate.
Convenient diastereospecific synthesis of a rociverine precursor and its resolution by lipase-catalyzed transesterification
DI BUSSOLO, VALERIA;CATELANI, GIORGIO;
1996-01-01
Abstract
Racemic cyclohexyl(hydroxymethyl)cyclohexanol I (R = H), a precursor of the antimuscarinic drug Rociverine, was obtained diastereospecifically in very high yield, from the Grignard reaction between C6H11MgCl and an appropriately protected 2-(hydroxymethyl)cyclohexanone. The prepn. of enantiomerically enriched (+)-(1R,2S)-(hydroxymethyl)cyclohexanol II and the corresponding 2-acetoxymethyl deriv. (+)-(1S,2R)-I (R = Ac) was achieved by lipase PPL-catalyzed transesterification of racemic I (R = H) with vinyl acetate.File in questo prodotto:
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