Preparation of cis-4-o-protected-2-cyclopentenol derivatives

Details Preparation of cis-4-o-protected-2-cyclopentenol derivatives Preparation of cis-4-o-protected-2-cyclopentenol derivatives

C - Chemistry, Metallurgy

07

C

C07C 43/196 (2006.01) C07B 53/00 (2006.01) C07C 41/26 (2006.01) C07C 319/20 (2006.01) C07C 323/12 (2006.01) C07D 307/20 (2006.01) C07D 309/12 (2006.01) C07D 333/32 (2006.01) C07D 335/02 (2006.01) C07F 7/08 (2006.01) C07F 7/18 (2006.01) C12P 7/02 (2006.01) C12P 7/22 (2006.01) C12P 9/00 (2006.01) C12P 11/00 (2006.01) C12P 17/00 (2006.01) C12P 41/00 (2006.01)

Patent

CA 2216245

The present invention relates to a novel process for preparing cis-4-O- protected-substituted-2-cyclopentenol derivatives comprising, (a) dissolving a 4-O-protected-2-cyclopentenone in a suitable organic solvent; and (b) treating the solution with a suitable Lewis acid and a suitable reducing agent at a temperature of from about -100 ~C to about 20 ~C. The cis-4-O-protected- substituted-2-cyclopentenol derivatives are useful intermediates in the preparation of various cyclopentanyl and cyclopentenyl purine analogs which are useful as immunosuppressants and in the preparation of various prostaglandins.

La présente invention se rapporte à un nouveau procédé de préparation de dérivés de cis-4-O-protégé-substitué-2-cyclopentenol, comprenant les étapes consistant: a) à dissoudre un 4-O-protégé-2-cyclopenténone dans un solvant organique approprié; et b) à traiter la solution avec un acide de Lewis ainsi qu'avec un agent réducteur appropriés, à une température comprise entre environ -100 ·C et 20 ·C. Ces dérivés sont utiles en tant qu'intermédiaires dans la préparation de divers analogues puriques de cyclopentanyle et de cyclopentényle, lesquels sont utiles en tant qu'immunosuppresseurs et dans la préparation de plusieurs prostaglandines.

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