FIELD: chemistry.
SUBSTANCE: invention relates to improved methods of producing 6-methyleneandrost-4-ene-3,17-dione and 6-methyleneandrost-1,4-diene-3,17-dione (MNN exemestane) using the obtained 6-methyleneandrost-4-ene-3,17-dione. 6-methyleneandrost-4-ene-3,17-dione is obtained using a method involving preliminary enolisation of Δ4-3-ketofunction of androst-4-ene-3,17-dione with formation of 3-alkoxyandrost-3,5-dien-17-one, subsequent three-component condensation with a secondary amine and formaldehyde in the medium of a polar protonic solvent, deamination of the N,N-disubstituted amino group to form a 6-methylene group in the medium of an aprotic solvent. 6-methyleneandrost-1,4-diene-3,17-dione is obtained through 1,2-dehydrogenation of 6-methyleneandrost-4-ene-3,17-dione via microbiological transformation in a medium containing up to 40% water-miscible aprotic solvent using Nocardioides simplex cells VKM As-2033D.
EFFECT: high output and selectivity under mild conditions for carrying out the process.
11 cl, 4 ex, 1 tbl
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Authors
Dates
2011-07-27—Published
2010-03-04—Filed