Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1981-03-26
1982-05-11
Roberts, Elbert L.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
26039745, C07J 100
Patent
active
043292941
ABSTRACT:
In accordance with the present invention, 17.alpha.-hydroxy-20-ketosteroids are prepared by the oxidation of 20-ketosteriods, such as 3-methoxy-pregna-3,5-dien-20-one. The 3-methoxypregna-3,5-dien-20-one is prepared from progesterone by methods well known in the art. The pregn-20-ones, such as 3-methoxypregna-3,5-dien-20-one, are oxidized with oxygen or air using a base catalyst in the presence of a phosphite reducing agent in a suitable solvent. The base catalyst consists of an alkali metal tert-alkoxide, which can be prepared from an alkali metal and a tert-alkanol. The oxidation reaction can be carried out at any temperature from about -20.degree. C. to about 50.degree. C. and for a period of 2-20 hours depending on the temperature at which the reaction is carried out. For example, at ambient temperature the rate of oxidation is sufficiently fast to complete the oxidation in 2 to 4 hours. This method for preparing 17.alpha.-hydroxy-20-ketosteroids from 20-ketosteroids is an important and valuable step in preparing corticosteroids and other hormones.
REFERENCES:
"Gardner et al.", The Journal of Organic Chemistry, (1968), No. 33, pp. 3294-3297.
Eastman Kodak Company
Reece III Daniel B.
Roberts Elbert L.
Tootle Clyde L.
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