Process for preparing 17.beta.-carboxy-5-androsten-3-ones

Details Process for preparing 17.beta.-carboxy-5-androsten-3-ones Process for preparing 17.beta.-carboxy-5-androsten-3-ones

1978-04-13

1979-12-18

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602395, C07J 900

Patent

active

041794532

ABSTRACT:
A process for preparing 17.beta.-carboxy-4-androsten-3-ones comprising the steps of (1) reacting a 17.beta.-(1-ketoethyl)-5-androsten-3-ol, for example, pregnenolene, with pyridine and iodine to form a pyridinium iodide compound; (2) reacting the pyridinium iodide compound with alkali metal methoxide in methanol to form a methyl-5-androsten-3-ol-17.beta. carboxylate; (3) oxidizing the product of Step (2) preferably with aluminum isopropoxide to form methyl-4-androsten-3-one-17.beta.-carboxylate; and (4) hydrolyzing the product of Step (3) to the corresponding 17.beta.-carboxylic acid, salt, or ester. The 17.beta.-carboxy-4-androsten-3-ones are useful as intermediates for preparation of N-substituted-17.beta.-carbamoylandrost-4-en-3-one and 4-aza-17.beta.-substituted-5.alpha.-androstan-3-one 5.alpha. reductase inhibitors.

REFERENCES:
King et al., "J. Am. Chem. Soc.", vol. 66, (1944), p. 1612.
"Organic Reactions in Steroid Chemistry", by Fried et al., p. 148.

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