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US 5,516,922 AGranted
Process for the preparation of 10(2-propynyl)estr-4-ene-3,17-dione
AssigneeMerrell Pharmaceuticals Inc.
InventorCynthia L. Rand
Life of this patent
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Abstract
This invention relates to a process for the preparation of 10-(2-propynyl)-estr-4-ene-3,17-dione, whereby this compound is synthesized utilizing ketals prepared from the addition of 2,2-dimethyl-1,3-propanediol to the starting compound, 19-norandrost-5(10)-ene-3,17-dione (NAD). A new process for the addition of the propynyl group to steroid epoxides by means of higher order cuprates is also described herein.
Claims2
A process for the preparation of 10-(2-propynyl)-estr-4-ene-3, 17-dione which comprises:
- a) reacting (58,108)-5, 10-epoxy-3,3,17,17-bis(2,2-dimethyltrimethylenedioxy)-19-norandrostane with a mixed higher order trialkylsilyl protected 2-propynyl copper dilithium reagent having three organic substituents, one of which is trimethylsilyl, with the others selected from the group consisting of thienyl and methyl, in tetrahydrofuran to yield the bisgemdimethyl ketal, 10-[3-(trialkylsilyl)-2-propynyl]-3,3,17,17-bis(2,2-dimethyltrimethylenedi oxy)-19-norandrostan-5-ol, and
- b) reacting 10-[3-(trialkylsilyl)-2-propynyl]-3,3,17,17-bis(2,2-dimethyltrimethylenedi oxy)-19-norandrostan-5-ol with base and with acid to yield 10-(2-propynyl)-estr-4-ene-3, 17-dione.
Dependencies are inferred from the claim text.