New process for manufacturing derivatives of 17 alpha-hydroxy 19

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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2603974, C07J 100

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active

047203579

ABSTRACT:
A process for making a known 6-methyl, 19-nor-pregna-4, 6-diene, 3.20-dione which begins with formylating a 3-alcoxy, 19-nor-pregna-3,5,17(20)-triene at the 6 position. The 6-formylated derivative is reduced to yield a 6-hydroxy methylated derivative, which is in turn dehydrated to a 3-keto, 6-methylenic derivative. The 3-keto derivative is then isomerized to a 3-keto, 4,6,17-pregnatriene. This latter triene is then coverted to the known product by reaction with a bis-hydroxylating agent and a catalyst based on osmium tetroxide. Optionally, the product can be acylated at the 17-alpha position. The process reduces the cost of producing the known product by allowing it to be manufactured from starting materials less costly than those previously required.

REFERENCES:
patent: 3314944 (1967-04-01), Diassi et al.
patent: 3726864 (1973-04-01), Phillipps et al.
patent: 4224320 (1980-09-01), Dahl et al.

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