Water → HCID 69840849, compound

Participants

Reaction Steps

tert-Butyl (3R)-3-aminopyrrolidine-1-carboxylate 6-2 (1.813 g, 9.73 mmol) was dissolved in 10 mL CH2Cl2. A solution of methylisocyanate (0.555 g, 9.73 mmol) in 10 mL CH2Cl2 was added. The solution was stirred for 3.5 hours. 50 mL H2O was added and the precipitate was extracted with CH2Cl2 (2×). The combined organic layers were dried (Na2SO4), filtered, and concentrated to afford tert-butyl (3R)-3-{[(methylamino)carbonyl]amino}pyrrolidine-1-carboxylate 6-3 as a white semi-solid. Free base: 1H NMR (DMSO-d6) δ 6.15 (bs, 1H), 5.63 (bd, 1H, J=4.22 Hz), 4.02 (m, 1H), 3.42-3.34 (m, 1H), 3.28-3.19 (m, 2H), 2.93-2.98 (m, 1H), 2.53 (d, 3H, J=4.58 Hz), 1.99-1.93 (m, 1H), 1.68-1.63 (m, 1H), 1.39 (s, 9H).

Provenance & Evidence