METHOD FOR PRODUCING (2R,3R,4R,5S)-1-BUTYL-2-(HYDROXYMETHYL)PIPERIDINE-3,4,5-TRIOL Russian patent published in 2021 - IPC C07D211/46 

FIELD: chemistry; pharmaceutics.

SUBSTANCE: invention relates to the field of chemistry and the chemical and pharmaceutical industry, namely to a method for producing substance of miglustat of ((2R,3R,4R,5S)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol), which includes the interaction of 2,3,4,6-tetra-O-benzyl-D-glucopyranose with sodium borohydride in a mixture of dichloromethane and methanol, to obtain 2,3,4,6-Tetra-O-benzyl-D-glucitol, which is extracted with ethyl acetate and, after drying and evaporation of an organic layer, purified from traces of water by azeotropic distillation with toluene; sequential oxidation of 2,3,4,6-Tetra-O-benzyl-D-glucitol with a mixture of dimethyl sulfoxide (DMSO) and phosphorus oxide P₂O₅ to form a 1,5-dicarbonyl derivative, purification of the specified derivative with diethyl ether and its reductive amination using sodium cyanoborohydride; purification by recrystallization from methanol obtained by the amination reaction of 2,3,4,6-Tetra-O-benzyl-N-butyl-1,5-dideoxy-1,5-D-glucitol; its interaction with hydrogen in the presence of palladium as a catalyst, deposited on activated carbon at a hydrogen pressure equal to one atmosphere, to form (2R,3R,4R,5S)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol with subsequent purification of the target product with silica gel.

EFFECT: high yield of stable miglustat substance.

1 cl, 10 dwg, 1 ex