Triethylamine → HCID 69241548, compound

Participants

Reaction Steps

To a stirred solution of (2S, 4R)-4-aminomethyl-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.51 mmol, Example 39C) in dichloromethane (2 mL) at room temperature was added cyclohexanecarbonyl chloride (0.092 g, 0.65 mmol) and triethylamine (0.10 mL, 0.75 mmol). The mixture was stirred at room temperature for 12 hours, concentrated under reduced pressure and the residue taken up in water and extracted with ethyl acetate (2×). The combined ethyl acetate layers were washed consecutively with saturated aqueous NaHCO3, 10% KHSO4 (aq), brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography with 30-40% ethyl acetate:hexane to provide the title compound. MS (CI) m/z 408 (M+1)+; 1H NMR (300 MHz, CDCl3) δ ppm 4.40-4.28 (m, 1 H), 3.88-3.66 (m, 2 H), 3.56-3.25 (m, 4 H), 3.22-3.16 (m, 2 H), 2.57 (m, 2 H), 2.55 (m, 1 H), 1.99-1.61, (m, 13 H), 1.41 (m, 9 H), 1.51 (m, 2 H).

Provenance & Evidence