Process for the manufacture of steroid carboxylic acid lactones

C - Chemistry – Metallurgy – 07 – J

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260/21, 260/37

C07J 21/00 (2006.01) C07J 17/00 (2006.01) C07J 31/00 (2006.01)

Patent

CA 1065849

PROCESS FOR THE MANUFACTURE OF STEROID CARBOXYLIC ACID LACTONES Abstract of the Disclosure An advantageous method for the manufacture of steroidal lactones of the spironolactone and canrenone type involves the following reactions sequence : bromination of a 3.beta.,17= dihydroxy- 17.alpha.-pregn-5-en-21-aldehyde in basic or neutral medium, oxidation of the 5,6-dibromo compound with hexavalent chromium compounds under basic or neutral conditions, dehydro- bromination 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.

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