Triethylamine → tert-Butyl [4-(hydroxymethyl)benzyl]carbamate

Participants

Reaction Steps

To a stirred solution of 4-[N-(t-butoxycarbonyl)-aminomethyl]benzoic acid (16.5 g, 65 mmol) and triethylamine (10 mL, 71 mmol) in dry THF (500 mL) at 0° C. was added ethyl chloroformate (7.5 mL, 78 mmol) dropwise. After stirring for 15 min, sodium borohydride (6 g, 159 mmol) was added in one portion and the reaction was allowed to warm to RT and stirred for 16 h. The reaction was cooled in an ice bath and carefully quenched with 1N hydrochloric acid, extracted with ethyl acetate, and the organic phase was washed with brine, dried (magnesium sulfate), and concentrated. The residue was purified by flash chromatography (silica gel, 20% ethyl acetate:chloroform) to give the title compound (10.07 g, 65%) as a white solid. TLC Rf 0.31 (20% ethyl acetate:chloroform); 1H NMR (CDCl3) δ1.46 (9H, s), 3.28 (1H, br s), 4.27 (2H, d, J=6 Hz), 4.65 (2H, s), 5.04 (1H, br s), 7.30 (4H, dd).

Provenance & Evidence