C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 401/00 (2006.01)
Patent
CA 2477543
A method of making 1.alpha.-hydroxy-2-methylene-19-norhomopregnacalciferol. The method includes the steps of condensing a bicyclic ketone with an allylic phosphine oxide to produce a protected 19-norpregnacalciferol analog, thereafter cleaving the protecting group to form 22-alcohol, converting the alcohol to an ester, reducing the ester to 17.beta.-isopropyl-19-nor-vitamin D analog, and finally deprotecting the 17.beta.-isopropyl derivative to form the desired compound. (see above formula)
L'invention concerne un procédé de fabrication de 1.alpha.-hydroxy-2-méthylène-19-nor-homoprégnacalciférol. Ce procédé consiste à condenser une cétone bicyclique avec un oxyde de phosphine allylique en vue de produire un analogue de 19-nor-prégnacalciférol protégé, puis à couper le groupe protecteur de manière à former un alcool 22, à convertir cet alcool en ester, à réduire l'ester en analogue de 17.beta.-isopropyl-19-nor-vitamine D, et enfin à déprotéger le dérivé de 17.beta.-isopropyle de façon à former le composé souhaité.
Deluca Hector F.
Gowlugari Sumithra
Sicinski Rafal R.
Borden Ladner Gervais Llp
Wisconsin Alumni Research Foundation
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