Hydrochloric Acid → HCID 74931419, compound

Participants

Reaction Steps

To a solution of racemic(2′R, 3R, 4′S)-2′-[5-bromo-2-(4-methoxycarbonyl-phenoxy)-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione prepared in Example 50c(0.8 g, 1.2 mmol) in tetrahydrofuran (20 mL) was added an aqueous solution (1 M) of NaOH (10 mL, 10 mmol) and methanol (10 mL). The reaction mixture was stirred at room temperature for 18 h, then acidified to “pH” 2 with concentrated aqueous HCl solution. The mixture was concentrated, partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried over MgSO4, and concentrated to give racemic(2′R, 3R, 4′S)-2′-[5-bromo-2-(4-hydroxycarbonyl-phenoxy)-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.6 g, 74%).

Provenance & Evidence