Medrogestone production

Details Medrogestone production Medrogestone production

1995-03-14

1996-05-21

Prior, Kimberly J.

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

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

C07J 700, C07J 7500

Patent

active

055191533

ABSTRACT:
A process for the production of 6,17.alpha.-dimethylpregna-4,6-diene-3,20-dione which comprises isolating 3.beta.,5.alpha., 6.beta.-trihydroxy- 6.alpha.,17.alpha.- dimethylpregnan-20-one monomethanolate from the solution of a Grignard reaction product of 3.beta.,5.alpha.-dihydroxy -17.alpha.-methyl-17.beta.-carbomethoxyandrostane-6-one and a methylmagnesium halide by solvent displacement with methanol; oxidizing the monomethanolate to the 3,20-dione; dehydrating the said 3,20-dione to the 4-ene-3,20-dione; dehydrating the 4-ene-3,20 dione; removing a 6-methylene-4-ene-3,20-dione byproduct and isolating the desired product.

REFERENCES:
patent: 3170936 (1965-02-01), Morand et al.
patent: 5428151 (1995-06-01), Winkley et al.
Deghenghi et al., J. Med. Chem., 6, 301 (1963).
Yadav et al., Syn. Commun., 19 (5&6), 1057 (1989).
Carruthers et al., J. Org. Chem., 57, 961 (1992).
Posner et al., Tet. Letts., 32(45), 6489 (1991).
Graber et al., J. Org. Chem., 27, 2534 (1962).
Bernstein et al., J. Org. Chem., 26, 269 (1961).

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