FIELD: chemistry.
SUBSTANCE: invention relates to a novel compound - 7α-(1-hydroxy-2,2,2-trifluoroethyl)-17-methyl-3,6-dimethoxy-4;5α-epoxy-6α,14α-ethenoisomorphinane of formula (1) which is a precursor of fluorine-containing tevinol, tevinols and orvinols, and can be used in production thereof, as well as a method of producing a compound of formula (1) in form of a mixture of (20R)- and (20S)-isomers, which involves reacting an aldehyde of formula
with a Ruppert-Prakash reagent [CF3Si(CH3)3], in the presence of a fluoride ion source such as tetrabutylammonium fluoride, in a solvent such as tetrahydrofuran, followed by treatment with and acid and separating the end product using known techniques. Separate (20R)- and (20S)-isomers are separated chromatographically.
EFFECT: improved method.
3 cl, 4 ex
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Authors
Dates
2014-01-10—Published
2012-08-21—Filed