Process for the synthesis of the hydroxyacetyl side-chain of ste

Details Process for the synthesis of the hydroxyacetyl side-chain of ste Process for the synthesis of the hydroxyacetyl side-chain of ste

1982-02-03

1984-01-03

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603971, 2603974, 26039745, 26039747, 424241, C07J 3300, C07J 500

Patent

active

044241593

ABSTRACT:
The present invention relates to a novel general process for synthesizing a .alpha.- or .beta.-oriented hydroxyacetyl side chain of steroids of the pregnane type, which comprises treating a corresponding steroid carbaldehyde in succession with formaldehyde dimethylmercaptal-S-oxide in the form of an alkali metal salt thereof, and with a strongly acid hydrolysing agent.
Preferred final products are compounds of the formula ##STR1## wherein n is 1 or 2, R.sup.2 represents methyl or difluoromethyl, and R.sup.1 represents hydroxymethyl, methoxymethyl, acetoxymethyl or hydrogen, and, if n is 2 and/or R.sup.2 is difluoromethyl, R.sup.1 also represents methyl. These compounds act as agonists or antagonists of natural steroid hormones. The antigestagenic 19,21-dihydroxy-17.alpha.-pregn-4-ene-3,20-dione and its 6,7-dehydro derivatives and diacetates are of particular interest.

REFERENCES:
patent: 3039926 (1962-06-01), Shull
patent: 3250792 (1966-05-01), Wettstein et al.
patent: 4155923 (1979-05-01), Neef et al.
Fieser & Fieser, "Steroids", pp. 566-567.
Helv. Chim. Acta 23 (1940), C. W. Shoppe, p. 927.
Journ. Amer. Chem. Soc. (1954), vol. 76, pp. 2026-2027.
Chemical Abstracts, vol. 85, 1976, p. 568.
Ogura et al., Tetrahedron Letters, 2681-2684 (1972).

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