4-Methylmorpholine → HCID 74931453, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of racemic(2′R, 3R, 4′S)-2′-[5-bromo-2-(4-fluorocarbonyl-phenoxy)-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.18 g, 0.28 mmol) in tetrahydrofuran (20 mL) was added 2-amino-2-methyl-propan-1-ol (0.2 g, 2.24 mmol), N-methylmorpholine (0.2 g, 2 mmol) and 4-dimethylaminopyridine (3 mg, 0.025 mmol). The reaction mixture was heated under nitrogen at 100° C. for 1 h, then cooled to room temperature. The mixture was diluted with ethyl acetate, washed with 1N HCl aqueous solution and H2O. The organic layer was separated, dried over Na2SO4 and concentrated. The residue was purified by chromatography (MeOH:EtOAc=1:19) to give racemic(2′R, 3R, 4′S)-2′-{5-Bromo-2-[4-(2-hydroxy-1,1-dimethyl-ethylcarbamoyl)-phenoxy]-phenyl}-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield: 84 mg, 42%).

Provenance & Evidence