Production of 1.alpha.-hydroxy vitamin d3

C - Chemistry – Metallurgy – 07 – J

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260/60, 204/91.0

C07J 9/00 (2006.01) C07J 41/00 (2006.01)

Patent

CA 1055484

ABSTRACT OF THE DISCLOSURE A process for the production of 1.alpha.-hydroxy provitamin D3 which comprises treating 1.alpha.,2.alpha.-epoxy-cholests-4,6-diene- 3-one at a low temperature with liquid ammonia; with ammonium chloride and with lithium metal to produce 1.alpha.,3.beta.- -dihydroxycholest-6-ene, converting this to the corresponding 1.alpha.,3.beta.-di(lower alkanoyl) derivative, reacting the latter with bromine to give 1.alpha.,3.beta.-di(lower alkanoyloxy) 6.beta.,7.alpha.- dibromocholestane, which is dehydrobrominated at give 1.alpha.,3.beta.-di(lower alkanoyloxy)-cholesta-5,7-diene, which is converted to the desired provitamin. The 1.alpha.,3.beta.-di(lower alkanoyloxy)cholest-6-ene can be oxidized to the corresponding 5-ene-7-one, which is converted to the 7-p-toluenesulfonyl hydrazone derivative, which is converted to the 1.alpha.-hydroxy provitamin D3 di(lower alkanoyloxy) derivative or to the 1.alpha.-hydroxy provitamin D3. Novel compounds are 1.alpha.,3.beta.- dihydroxy-cholest-6-ene, its di(lower alkanoyloxy) derivative; 1.alpha.,3.beta.-di(lower alkanoyloxy)-6.beta.,7.alpha.-dibromocholestane; 1.alpha.,3.beta.-diacetoxycholest-5-ene-7-one and the corresponding 7-p-toluenesulfonylhydrazone derivative.

238027

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