Sodium cyanoborohydride → HCID 44828772, compound

Participants

Reaction Steps

To a solution of (3R)—N-(2-oxo-2-{[3-(trifluoromethyl)phenyl]amino}ethyl)pyrrolidine-3-carboxamide hydrochloride (130 mg, 0.370 mmol) in MeOH (1 mL) was added methyl 4-(4-oxopiperidin-1-yl)benzoate (95 mg, 0.407 mmol) and NaBH3CN (70 mg, 1.11 mmol). After overnight, the mixture was washed with EtOAc and NaHCO3 (sat. aq.), the organic phase was dried over MgSO4, concentrated, and subjected to flash chromatography (EtOAc) to generate the title compound as a white solid (45% yield, 2 steps). 1H-NMR (CDCl3) δ: 1.55-1.75 (m, 2H), 1.85-2.06 (m, 3H), 2.10-2.22 (m, 1H), 2.24-2.40 (m, 1H), 2.42-2.62 (m, 2H), 2.81-3.02 (m, 5H), 3.65-3.85 (m, 5H), 4.05-4.20 (m, 2H), 6.81 (d, J=8.9 Hz, 2H), 7.20-7.40 (m, 2H), 7.65-8.00 (m, 5H), 9.57 (s, 1H). MS m/z: 533 (M+1)

Provenance & Evidence