Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

Participants

Reaction Conditions

Reaction Steps

2-Aminoethanol (20 g.) and sodium carbonate (84.8 g.) is dissolved in acetone-water (1:1) (500 ml.) and benzylchloroformate (83.9 g.) is added dropwise to the stirred solution at 0° C. over a period of 0.5 hours. The mixture is stirred at 0° C. for a further 2.5 hours. The solids are filtered off and washed with acetone and the filtrate is evaporated to dryness. The resulting gum is taken up in chloroform and filtered. The filtrate is evaporated to dryness. The residue is chromatographed on a silica gel column (140×5 cm.) using chloroform and then 10% methanol in chloroform as the eluant to give 2-benzyloxycarbonylaminoethanol, which crystallizes from hexane as colorless needles; m.p. 53°-55° C.; γ max (CCl4) 3450, 3325, 1720, 1510, 1245 cm-1 ; δ (CDCl3) 3.29 (2H, m HOCH2CH2NH--), 3.57 (2H, m, HOCH2CH2NH--), 5.07 (2H, s, --CH2C6H5) and 7.31 ppm (5H, s, --CH2C6H5).

Provenance & Evidence