Process for production of 1-.alpha., 3-.beta., 24-trihydroxy .DE

Details Process for production of 1-.alpha., 3-.beta., 24-trihydroxy .DE Process for production of 1-.alpha., 3-.beta., 24-trihydroxy .DE

1991-04-30

1992-05-26

Shen, Cecilia

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

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

C07J 900

Patent

active

051170159

ABSTRACT:
A process for producing a 1.alpha.,3.beta.,24-trihydroxy-.DELTA..sup.5 -steroid represented by the formula (II): ##STR1## wherein R.sub.1 and R.sub.2, independently, represent a hyrogen atom, or R.sub.1 and R.sub.2 together form a single bond, R.sub.3 represents an unsubstituted or halogen-substituted lower alkyl, and R.sub.4 represents a hydrogen atom, hydroxy or a protected hydroxy, comprising reducing a 1.alpha.,2.alpha.-epoxy-.DELTA..sup.4,6 -3,24-dioxosteroid represented by the formula (I) ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the same meanings as defined in formula (II), using an alkaline metal or alkaline earth metal and a proton donor in a solvent comprising ammonia or amine characterized in that at an early stage of the reaction, the 1.alpha.,2.alpha.-epoxy-.DELTA..sup.4,6 -3,24-dioxosteroid is reacted with the alkaline metal or alkaline earth metal in the presence of a proton acceptor, and then at a later stage of the reaction, a resulting intermediate product is reacted with the proton donor.

REFERENCES:
patent: 3901928 (1975-08-01), Hesse et al.
patent: 3907843 (1975-09-01), De Luca et al.
patent: 3966777 (1976-06-01), Mazur et al.
patent: 4022891 (1977-05-01), Takeshita et al.
patent: 4305881 (1981-12-01), Furst et al.
patent: 4670190 (1987-06-01), Hesse et al.
Journal of the Chemical Society. Perkin Transactions i, No. 14, Sep. 1975, pp. 1421-1424, Washington, US; M. Morisaki et al.

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