Dimethylformamide → tert-butyl N-[2-(3-aminophenoxy)ethyl]carbamate

Participants

Reaction Steps

A mixture of 1-aminophenol (1) (207 mg, 1.9 mmol), 2-(tert-butoxycarbonylamino)ethyl 4-methylbenzenesulfonate (2) (500 mg, 1.9 mmol), and cesium carbonate (770 mg, 2.2 mmol) in DMF (6 ml) was stirred at room temperature under argon for 15 hours. The mixture was concentrated under reduced pressure. The residue was partitioned between EtOAc and water. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (40 to 60% EtOAc-hexanes gradient) gave tert-butyl 2-(3-aminophenoxy)ethylcarbamate (3) as colorless oil. Yield (220 mg, 58%). 1H NMR (400 MHz, DMSO-d6) δ 6.92 (t, J=5.2 Hz, 1H), 6.85 (t, J=8.0 Hz, 1H), 6.08-6.12 (m, 2H), 6.02-6.04 (m, 1H), 4.99 (bs, 2H), 3.79 (t, J=6.0 Hz, 2H), 3.21 (q, J=6.0 Hz, 2H), 1.36 (s, 9H).

Provenance & Evidence