Ethanolamine → 4-Acetoxybenzyl 2-hydroxyethylcarbamate

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Crude 61 (from 321 mg of 60, max 1.9 mmol) was taken up in 8 mL of CH2Cl2 and the solution was added to a mixture of ethanolamine (140 μL, 2.3 mmol) and triethylamine (540 μL, 3.9 mmol) in 7 mL of CH2Cl2 cooled in an ice bath. The mixture was stirred in the same bath, which was left unmaintained. After 4 h, it was diluted with 100 mL of ethyl acetate and washed with 50 mL of each of 1% HCl in 2/3 saturated brine, 2/3 saturated brine and saturated aqueous NaHCO3 (twice). The organics were dried over Na2SO4 and concentrated in vacuo to furnish 62 (364 mg, 1.44 mmol, 76% over two steps) as a gum. 1H NMR (400 MHz, CDCl3) δ 2.30 (s, 3H), 3.35 (broad q, J=5.2 Hz, 2H), 3.72 (broad q, J=5.2 Hz, 2H), 5.09 (s, 2H), 5.15 (broad s, 1H), 7.07 (d, J=8.5 Hz, 2H), 7.37 (d, J=8.4 Hz, 2H).

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