A process for making epoxide intermediates

Details A process for making epoxide intermediates A process for making epoxide intermediates

C - Chemistry, Metallurgy

07

C

C07C 405/00 (2006.01)

Patent

CA 2303797

It has been surprisingly discovered that the disadvantages of the lengthy literature procedures to synthesize 13,14-dihydro prostaglandin A, E, and F derivatives can be overcome using a novel Methyl 7-(2-hydroxy-5-(2-(2- oxiranyl)ethyl)-4-(1,1,2,2tetramethyl-1-silapropoxy)cyclopentyl) heptanoate intermediate, which can be synthesized from commercially available Methyl 7-[3- (R)-hydroxy-5-oxo-1-cyclopent-1-yl] heptanoate. This novel intermediate can be coupled with oxygen, carbon, sulfur, and nitrogen nucleophiles, in the presence of a base or a Lewis acid, in a ring-opening process to provide 13,14- dihydro prostaglandin A, E, and F derivatives.

On a découvert avec surprise que les inconvénients des longues procédures actuellement documentées pour synthétiser les dérivés 13,14-dihydro de prostaglandine A, E et F peuvent être éliminés grâce à un intermédiaire d'heptanoate de méthyle 7-(2-hydroxy-5-(2-(2-oxiranyl)éthyl)-4-(1,1,2,2-tétraméthyl-1-silapropoxy)cyclopentyl), qui peut être synthétisé à partir d'heptanoate de méthyle 7-[3-(R)-hydroxy-5-oxo-1-cyclopent-1-yl] disponible dans le commerce. Ce nouvel intermédiaire peut être couplé à des nucléophiles d'oxygène, de carbone, de soufre et d'azote, en présence d'une base ou d'un acide de Lewis, dans un procédé à ouverture de cycle, pour fournir des dérivés 13,14-dihydro de prostaglandine A, E et F.

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