CRYSTALS OF 6,7-UNSATURATED-7-CARBAMOYLMORPHINANE DERIVATIVES AND METHOD OF THEIR PRODUCTION Russian patent published in 2018 - IPC C07D489/08 C07D271/06 

FIELD: chemistry.

SUBSTANCE: invention relates to the method of producing a compound of the formula (II), where R^lb is a hydroxyl protecting group selected from the group consisting of acetyl, formyl, benzoyl, chloroacetyl, pivaloyl, methylcarbonate, isobutylmalonate, benzylmalonate, vinylcarbene, phenylcarbamate, mesyl, and tosyl, R² is a C1-6alkyl, substituted cyclopropyl, and R³ is a C1-6alkyl, substituted oxadiazol, which is substituted by phenyl, or pyrimidine substituted C1-6alkoxy including the interaction of the compounds of the formula (III), where R^lb and R² have the above values, in the presence or in the absence of an acid compound of the formula R³-N=C=O, where R³ has the above significance, or with a compound of the formula R³-NH-C(=O)-X, where R³ has the above meanings, and X is a leaving group selected from the group consisting of phenoxy, p-nitrophenoxy, and o-nitrophenoxy. The invention relates to the method of producing a compound of the formula (I), where R² is cyclopropyl C1-6alkyl and R³ is C1-4alkyl substituted with oxadiazole which is substituted by phenyl or pyrimidine substituted with C1-4alkoxy including a base treatment with the compound of the formula (IIC) wherein R^1c is a hydroxyl protecting group removable by the base, and R² and R³ have the values indicated above. The invention also relates to a method of producing the compound of the formula (I). Additionally, the invention relates to the method of producing a compound of the formula (IX) and an intermediate compound of the formula (IID) where R¹ is a hydroxy-protective group selected from the group consisting of acetyl, formyl, benzoyl, chloroacetyl, pivaloyl, methylcarbonate, isobutylmalonate, benzylmalonate, vinylcarbene, phenylcarbamate, mesyl, and tosyl.

EFFECT: method of producing compounds of the formula I containing fewer steps.

19 cl, 19 tbl, 26 dwg, 2 ex