METHOD FOR STEREOSELECTIVE PRODUCTION OF ASYMMETRICAL DERIVATIVES OF OXINDOLE Russian patent published in 1997 - IPC

FIELD: organic synthesis. SUBSTANCE: desired derivatives have formula where R₁-CH₃, C₂H₅, C₆H₅, C₆H₅-CH₂, R is CN, CH₂NH₂.. Racemic mixture of oxindole having formula where R is as it mentioned above is used as reagent 1. Halogenated acetonitrile is used as reagent 2. Reaction is carried out at 5-30 C in two-phase system which contents hydroxide of alkaline metal in aqueous phase, aromatic hydrocarbon or halogenated aromatic solvent, origin oxindole and phase transfer catalyst. Thus obtained mixture of enantiomers comprising 68-90 % excess of one of enantiomers may be affected by catalytic reduction, the process is carried out in the presence of gaseous H₂. Thus treated mixture of enantiomers of primary amines is separated with the help of dibenzoyl-D-tartaric acid or ditoluoyl-D-tartaric acid followed by isolation thus prepared precipitate of salt and by its conversion into free base by treatment with base. EFFECT: improves efficiency of the method. 12 cl, 1 dwg, 1 tbl