Processes for preparation of steroid derivatives

Details Processes for preparation of steroid derivatives Processes for preparation of steroid derivatives

C - Chemistry, Metallurgy

07

J

260/60

C07J 9/00 (2006.01)

Patent

CA 1055015

ABSTRACT OF THE DISCLOSURE A process for the preparation of 1a-hydroxycholecal- ciferol characterized by reacting cholesta-1,5,7-trien-3.beta.-ol with a triazoline-3,5-dione to form a 1,4-cyclized adduct thereof, oxidizing the adduct with a peroxide to form the corresponding 1.alpha.,2.alpha.-epoxide, reducing said epoxide to cholesta- 5,7-diene-1.alpha.,3.beta.-diol which is then subjected to radiation with ultraviolet rays to give 1.alpha.,3.beta.-dihydroxyprevitamin D3 which is allowed to stand still in the dark thereby producing 1.alpha.-hydroxy- cholecalciferol. The cholesta-1,5,7-trien-3.beta.-ol used as starting material is valuable as an intermediate and is prepared by isomerizing cholesta-1,4,6-trien-3-one in the presence of a basic catalyst and reducing the resulting cholesta-1,5,7-trien-3-one with a metal boron hydride. The 1.alpha.-hydroxycholecalciferol has a much higher vitamin D-like biological activity than vitamin D2 or vitamin D3 and is valuable as a nutrition-promoting agent and as an anti-rachitic agent.

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