Reaction #1328394

Reaction equation

2-aminoethanol

benzyl chloroformate

→

title compound

Yield 66.0%

N-CBZ-2-aminoethanol

Yield 66.0%

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONAfter complete addition
2. 2
   Otherpurified by flash column chromatography on silica gel

Procedure

To 0° C. cold of CH2Cl2 solution (300 mL) of 2-aminoethanol (10.8 g, 0.177 mole) and TEA (26.8 g; 0.265 mole) was added slowly a CH2Cl2 solution (50 mL) of benzyl chloroformate (33.2 g, 0.194 mole). After complete addition, the resulting solution was gradually warmed to room temperature and stirring was continued at room temperature overnight. The reaction was worked up and purified by flash column chromatography on silica gel, affording 22.8 g in 66% yield of title compound. 1H NMR (CDCl3): δ 7.34-7.40 (m, 5H), 5.20-5.32 (m, 1H), 5.14 (s, 2H), 3.74 (q, 2H), 3.37 (q, 2H), 2.38 (bs, 1H).

Source