Process for preparing optically active epoxides

Details Process for preparing optically active epoxides Process for preparing optically active epoxides

C - Chemistry, Metallurgy

07

D

C07D 303/36 (2006.01) C07D 301/24 (2006.01)

Patent

CA 2400514

The invention concerns a process for the production of optically active epoxides useful as pharmaceutical intermediates, particularly in the field of HIV protease inhibitors. The optically active epoxides are produced in commercially acceptable yields from an optically active alcohols by a Mitsunobu reaction and a cyclisation step, preferably comprising an intermediate recrystallisation step. The stereochemistry of the alcohol is inverted during the Mitsunobu reaction to produce the desired epoxide.

Cette invention se rapporte à un procédé servant à produire des époxydes optiquement actifs utiles comme intermédiaires pharmaceutiques, notamment dans le domaine des inhibiteurs de VIH-protéases. Ces époxydes optiquement actifs sont produits en rendements commercialement acceptables à partir d'alcools optiquement actifs par une réaction de Mitsunobu et une phase de cyclisation, avec de préférence une phase de recristallisation intermédiaire. La stéréochimie de l'alcool est inversée pendant la réaction de Mitsunobu pour produire l'époxyde souhaitée.

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