1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 74931390, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of racemic(2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[2-(1-hydroxycarbonylmethyl-4-piperidinyloxy)-5-iodo-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (50 mg, 0.069 mmol) in anhydrous N,N-dimethylformamide (2 mL) was added EDCI (26.5 mg, 0.139 mmol), HOBT (18.8 mg, 0.139 mmol), diisopropylethylamine (35.9 mg, 0.278 mmol), NH4Cl (7.4 mg, 0.278 mmol). The reaction mixture was heated at 80° C. for 1 h, then cooled to room temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (MeOH:EtOAc=8:92) to give racemic(2′R, 3R, 4′S)-2′-[2-(1-carbamoylmethyl-4-piperidinyloxy)-5-iodo-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as an off white solid (Yield 25.6 mg, 51%)

Provenance & Evidence