Process for the preparation of 9(11)-dehydro steroids

Details Process for the preparation of 9(11)-dehydro steroids Process for the preparation of 9(11)-dehydro steroids

1988-06-10

1990-04-17

Lipovsky, Joseph A.

Organic compounds -- part of the class 532-570 series

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

552610, 552640, C07J 100

Patent

active

049178270

ABSTRACT:
9(11)-dehydroandrostanes and 9(11)-dehydropregnanes are prepared by dehydrating the corresponding 9-alpha-hydroxy steroid in the presence of a Lewis acid. The corresponding 8(9)-dehydro-isomer was not detectable. The resulting products are valuable intermediates in steroid synthesis especially in the preparation of corticosteroids.

REFERENCES:
patent: 3026337 (1962-03-01), Barton et al.
patent: 4102907 (1978-07-01), Shepard
patent: 4255344 (1981-03-01), Imada et al.
Batist et al., CA 109:129460y (1988).
Gist--Brocades, CA 109:129454z (1988).
Paryzek et al., CA 94:139982f (1981).
Wydra et al., CA 104:6045f (1986).
ApSimon et al., CA 94:13038j (1981).
Bergstrom et al., "Acid--Catalysed Rearrangement of 9--alpha--hydroxy--4--androstene--3,17--dione", Chemistry and Industry, 9/1961, pp. 1530-1531.
Carlson et al., "Lewis Acids in Organic Synthesis . . . ", Acta Chemica Scandinavica, 1986, pp. 522-533.
Fadel et al., "Anhydrous Ferric Chloride Adsorbed on Silica Gel . . . ", Tetrahedron, vol. 41, No. 2, 1985, pp. 413-420.

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