Process for the manufacture of steroid carboxylic acid lactones

Details Process for the manufacture of steroid carboxylic acid lactones Process for the manufacture of steroid carboxylic acid lactones

1978-07-20

1980-03-11

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26023955C, 2603975, C07J 7100

Patent

active

041928024

ABSTRACT:
An advantageous method for the manufacture of steroidal lactones of the spironolactone and canrenone type involves the following reaction sequence: bromination of a 3.beta. ,17-dihydroxy-17.alpha. -pregn-5-en-21-carboxaldehyde in basic or neutral medium, oxidation of the 5,6-dibromo compound with hexavalent chromium compounds under basic or neutral conditions, dehydrobromination with inorganic basic agents, such as lithium halides in the presence of lithium carbonate, or with organic bases, such as pyridine, oxidation of the steroid-4,6-diene compound so obtained having in the 17-position the same substituents as the starting material mentioned, with compounds of hexavalent chromium in acid solution, optionally after pretreatment with an acid or, in particular, with a thiocarboxylic acid (to introduce the 7.alpha.-acylthio group, e.g. if spironolactone is to be manufactured). The new process gives better yields than those hitherto described.

REFERENCES:
patent: 3413289 (1968-11-01), Gal et al.
patent: 3492292 (1970-01-01), Gal et al.
patent: 3738983 (1973-06-01), Dreyden, Jr. et al.
patent: 3847906 (1974-11-01), Radscheit et al.
patent: 3883512 (1975-05-01), Stache et al.

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