Methylamine → (R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamide

Participants

Reaction Steps

To (R)-1-(4-nitro-phenyl)-pyrrolidine-2-carboxylic acid (Method 55; 1.8 g, 7.6 mmol) in DCM (50 ml) was added HATU (3.2 g, 8.4 mmol) and DIPEA (2.0 ml, 11.4 mmol). The reaction was stirred for 10 minutes before the addition of methylamine (0.84 g, 15 mmol); the reaction was stirred for 1 hour and then quenched with water (50 ml). The reaction was extracted with DCM (3×100 ml), dried and solvent removed in vacuo to yield a yellow gum. Purification was achieved via column chromatography eluting with 20% EtOAc/isohexane, 60% EtOAc/isohexane and finally 100% EtOAc. The title compound was obtained as a yellow solid (1.4 g, 74%). NMR (299.954 MHz, CDCl3) δ 8.13 (d, 2H), 6.55 (d, 2H), 6.06 (s, 1H), 4.14 (t, 1H), 3.70 (t, 1H), 3.38 (q, 1H), 2.75-2.66 (m, 1H), 2.36-2.29 (m, 2H), 2.17-1.95 (m, 2H), 0.82-0.73 (m, 2H), 0.46-0.35 (m, 2H); m/z 276.

Provenance & Evidence