Process for preparing active compounds

Details Process for preparing active compounds Process for preparing active compounds

1978-05-19

1981-06-09

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603975, 26023955C, 2602395, C07J 100

Patent

active

042724457

ABSTRACT:
A process for the preparation of a compound of the formula (A): ##STR1## wherein: R.sub.3 is a C.sub.1-5 alkyl group, a C.sub.3-6 alkenyl group, a C.sub.3-6 cycloalkyl group or an alkylphenyl group in which the alkyl moiety contains 1 to 3 carbon atoms and the phenyl moiety is optionally substituted; R.sub.4 is a hydroxyl group, or a group OR.sub.6 wherein R.sub.6 is a C.sub.2-7 acyl group, a C.sub.1-4 alkyl group, or an optionally substituted benzyl group; R.sub.5 is hydrogen or a C.sub.1-5 alkyl group; or R.sub.4 and R.sub.5 together with the carbon atom to which they are joined represent a carbonyl group; which process comprises the reaction of a compound of the formula (C): ##STR2## wherein Q is a carbonyl group protected by a reagent capable of selectively protecting the 3-carbonyl of androstenedione, and R.sub.3, R.sub.4 and R.sub.5 are as defined in formula (A), to generate an unprotected carbonyl group in place of the protected carbonyl group Q.
This process has advantages over the known process for the preparation of compounds of formula (A).

REFERENCES:
patent: 3049555 (1962-08-01), Tyner
"Steroid Reactions" (1963) by Djerassi, pp. 48 and 49.
Organic Reactions in Steroid Chemistry, vol. 1, (1974) by Fried et al. pp. 393 and 394.

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