Process for the production of 1.alpha.-hydroxy provitamin D.sub.

Details Process for the production of 1.alpha.-hydroxy provitamin D.sub. Process for the production of 1.alpha.-hydroxy provitamin D.sub.

1975-10-15

1976-06-29

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26023955R, 424236, C07J 900

Patent

active

039667774

ABSTRACT:
A process for the production of 1.alpha.-hydroxy provitamin D.sub.3 which comprises treating 1.alpha., 2.alpha.-epoxy-cholesta-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 to 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 D.sub.3 di(lower alkanoyloxy) derivative or to the 1.alpha.-hydroxy provitamin D.sub.3. 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.

REFERENCES:
patent: 3739001 (1973-06-01), DeLuca
patent: 3929770 (1975-12-01), Ishikawa et al.

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