METHOD OF PREPARING 6-(N-METHYL-N-PHENYL)AMINOMETHYL-HYDROCORTISONE ESTERS THEREOF FROM HYDROCORTISONE 21-ACETATE Russian patent published in 2018 - IPC C07J5/00 C07J75/00 

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 6-(N-methyl-N-phenyl)aminomethyl-hydrocortisone (11β,17α,21-trihydroxy-6-(N-methyl-N-phenyl)aminomethylpregn-4-ene-3,20-dione) or esters thereof of general formula I

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in which R=COCF₃ or H; R₁=COCH₃ or H, from hydrocortisone 21-acetate of formula II, a sequence of transformations, including protection 11β-hydroxyl group by esterification with a trifluoroacetic acid derivative in an aprotic solvent medium under conditions of basic catalysis using an effective amount of a catalyst to form 21-acetoxy-17α-hydroxy-11β-trifluoroacetoxypregn-4-ene-3,20-dione of formula III, enol-esterification Δ⁴-3-keto system of the obtained compound by the action of a trialkyl orthoformate in the presence of an acid catalyst to form a 3-alkoxyester Δ^3,5-3-hydroxy derivative of general formula IV, condensing it with Mannich reagent, formed in situ from formaldehyde and N-methylaniline, in the presence of an acid catalyst and deprotection of 11β- and 21-hydroxyl groups by methods of chemical solvolysis completely (R=R₁=H) or partially (R=H; R₁=COCH₃).

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EFFECT: method has been developed for the preparation of compounds of formula I from hydrocortisone 21-acetate with the yield of the desired products of at least 85 %.

34 cl, 7 ex