Methanol → HCID 53475915, compound

Participants

Reaction Conditions

Reaction Steps

1-(2-(aminomethyl)-5-chlorophenyl)pyrrolidin-3-ol 2ai (1.18 g, 5.2 mmol) was dissolved in 40 ml of AcOEt and at 0° C. triphosgene (1.4 g, 5.2 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 10 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (674 mg, 4.52 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt 8/MeOH 2). The solvent was evaporated and the crude was dissolved in AcOEt (80 ml) and washed with water (1×40 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 390 mg of a pale pink solid. Yield=21% 1HNMR (DMSO, 200 MHz) δ 2.20 (2H, m), 3.33 (4H, m), 3.69 (2H, s), 4.29 (1H, b), 5.20 (1H, b), 6.62 (2H, m), 6.90 (4H, m), 7.27 (1H, d, J=8 Hz), 8.29 (1H, s), 9.95 (1H, bs), 10.60 (1H, bs); [M+1] 402.4 (C19H20ClN5O3 requires 401.85).

Provenance & Evidence