Process for preparing 21-lower alkoxyoxalylprogesterones

Details Process for preparing 21-lower alkoxyoxalylprogesterones Process for preparing 21-lower alkoxyoxalylprogesterones

1981-03-02

1982-04-20

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07J 700

Patent

active

043258786

ABSTRACT:
In accordance with the present invention, 21-lower alkoxyoxalylprogesterone is prepared in high yield by the lower alkoxyoxalylation of 3-methoxypregna-3,5-diene-20-one. The 3-methoxypregna-3,5-diene-20-one is prepared from progesterone by methods well known in the art. The 3-methoxypregna-3,5-diene-20-one is lower alkoxyoxalylated with an alkoxide base and the corresponding lower alkyloxalate in a suitable solvent. The alkoxide base consists of a lower alkoxide with an alkali metal counter ion. The lower alkyl group of both the alkoxide and oxalate should be the same and also are the same as the group to be added to the 21 position of the 20-keto steroid, the lower alkyl group contains 1 to 6 carbon atoms. The lower alkoxyoxalylation reaction can be carried at any temperature below the boiling point of the solvent and for a period of 2-20 hours depending on the temperature at which the reaction is carried out. For example, at elevated temperatures the rate of reaction is sufficiently fast to complete the lower alkoxyoxalylation in 2 to 4 hours whereas if the reaction is carried out at ambient temperatures complete reaction can require 14 to 20 hours. The reaction is preferably carried out under an inert atmosphere such as a nitrogen or argon atmosphere.

REFERENCES:
patent: 2698852 (1955-01-01), Beal et al.
Chem. Abstracts, 58 (1963), Pars. 3494c, article by Azioni et al. (British Pat. 893,365).

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