Process for preparing 9,11-unsaturated steroidal compound from the corresponding saturated steroidal compound
US4328162A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Sep 5, 1980 |
| Grant date | May 4, 1982 |
| Priority date | — |
| Expiry date | Sep 5, 2000 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07J7/004
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The present invention provides a non-fermentation process for placing unsaturation at the 9,11 position in a steroidal compound. Also, the present invention provides a process whereby the modified steroidal compound can be separated from the reaction mixture without the use of chromatography. More specifically, the present invention provides a process whereby a steroid compound such as 17-.alpha.-hydroxy-progesterone is reacted to form the meta iodoaryl benzoate. The iodoarylbenzoate is then irradiated with visible light in the presence of an alkyl-m-iodobenzoate dichloride to form the 9.alpha.-chloro steroid derivative. The chlorinated steroid derivative can then be hydrolized to provide a 9.alpha.-chloro steroidal alcohol and m-iodobenzoic acid. The m-iodobenzoic acid is extracted by the use of an aqueous base. The chlorinated steroidal alcohol can then be recovered and converted by conventional dehalogenation techniques to steroidal unsaturated compound having a double bond in the 9,11 position of the steroid nucleus. Alternatively, the chlorinated steroid derivative can be dehalogenation and then hydrolized.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.