The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Jun. 29, 1976
Filed:
Oct. 15, 1975
Yeda Research & Development Co. Ltd., Rehovot, IL;
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.