Triethylamine → 2-[(Bromoacetyl)(2-phenylethyl)amino]ethyl carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of bromoacetyl bromide (0.25 mL, 2.92 mmol) in CH2Cl2 (10 mL) at -10° C. was added a solution of 2-(phenylethylamino)ethyl carbamic acid tert-butyl ester (0.7 g, 2.65 mmol) and triethylamine (0.41 mL, 2.92 mmol) in CH2Cl2 (10 mL) dropwise. The mixture was stirred at -10° C. for 30 min, before removal of the solvent in vacuo. The residue was partitioned between EtOAc (2×30 mL) and water (30 mL). The combined organic layers were dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with petrol:EtOAc (2:1→1:1), to afford the title amide (0.81 g, 79%) as a colourless oil. 1H NMR (250 MHz, CDCl3) δ 1.44 (9H, s), 2.86-2.94 (2H, m), 3.10-3.94 (8H, m), 4.59 and 4.92 (1H, 2×br s), 7.15-7.37 (5H, m). MS (ES+) (385/387, M+).

Provenance & Evidence