Process for the manufacture of 6.beta.,7-methylene-3-oxo-4-ene s

Details Process for the manufacture of 6.beta.,7-methylene-3-oxo-4-ene s Process for the manufacture of 6.beta.,7-methylene-3-oxo-4-ene s

1977-03-29

1978-10-10

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26023955R, 2603974, 2603436, 2603478, C07J 7100

Patent

active

041196279

ABSTRACT:
The invention provides a novel general process for the manufacture of 6.beta.,7-methylene-3-oxo-4-ene-steroids by successively (a) reacting a 3.xi.,5.beta.-dihydroxy-6-ene-steroid which is optionally etherified or esterified in the 3-position with a zinc/copper-methylene iodide reagent to introduce the 6.beta.,7-methylene bridge, (b) liberating an etherified or esterified 3-hydroxyl group if such a group is present, (c) treating the resultant 6.beta.,7-methylene-3.xi.,5.beta.-dihydroxy-steroid with an oxidizing agent to dehydrogenate the 3-hydroxyl group to the oxo group, and (d) dehydrating the 6.beta.,7-methylene-5.beta.-hydroxy-3-oxo-steroid to form the 4,5-double bond. The starting materials, which form a novel class of compounds, can be obtained by a novel process by converting a 5.beta.,6-oxido-3.xi.-hydroxy-steroid with a selenol, for example phenylselenol, to a 6.alpha.-alkyl- or arylseleno-3.xi.,5.beta.-dihydroxy-steroid, oxidizing this compound with a peroxidic reagent, for example hydrogen peroxide, in a weakly acid medium to give the corresponding 6-selenonyl compound, and converting this compound, preferably by treatment with a base, preferably with 1,5-diazabicyclo[4,3,0]non-5-ene, to give the 3.xi.,5.beta.-dihydroxy-6-ene-steroid. During the course of these reactions, the 3-hydroxyl group is preferably temporarily protected by esterification or etherification.

REFERENCES:
patent: 3531503 (1970-09-01), Cereghetti et al.

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