Process for preparing 9,11-unsaturated steroidal compound from t

Details Process for preparing 9,11-unsaturated steroidal compound from t Process for preparing 9,11-unsaturated steroidal compound from t

1980-09-05

1982-05-04

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603972, C07J 500

Patent

active

043281621

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.

REFERENCES:
patent: 4061661 (1977-12-01), Kerb et al.
patent: 4252719 (1981-02-01), Breslow et al.
Breslow et al. "Journal of American Chem. Soc." (1977), vol. 99, No. 3, pp. 905-915.

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