Process for the production of 1.alpha.-hydroxy provitamin D.sub.3 and 1.alpha.-hydroxy vitamin D.sub.3
US3966777A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Oct 15, 1975 |
| Grant date | Jun 29, 1976 |
| Priority date | — |
| Expiry date | Oct 15, 1995 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07J41/0005
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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-toluenesulfon…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.