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Convenient diastereospecific synthesis of a rociverine precursor and its resolution by lipase-catalyzed transesterification |
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| Authors: | Valeria Di Bussolo Giorgio Catelani Ettore Mastrorilli Cristina Di Bugno Raffaello Giorgi |
| Affiliation: | Dipartimento di Chimica Bioorganica, Università di Pisa, Via Bonanno 33, 56126, Pisa, Italy Laboratori Guidotti S.p.A., Via Livornese 402, 56122, Pisa, Italy [Company related with “A. Menarini” Industrie Farmaceutiche Riunite S.r.l.] |
| Abstract: | (±)-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. |
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