Reaction #1328393

Reaction equation

benzyl chloroformate

3-aminopropanol

→

title compound

Yield 58.9%

N-CBZ-3-aminopropanol

Yield 58.9%

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   WashThe reaction mixture was washed with H2O
2. 2
   Otherdried
3. 3
   Otherpurified by flash column chromatography (on silica gel, CH3OH—CH2Cl2)

Procedure

A CH2Cl2 solution (300 mL) of 3-aminopropanol (10 g, 0.133 mole) and TEA (20 g, 0.2 mole) was cooled to 0° C., followed by slow addition of CH2Cl2 solution (25 mL) of benzyl chloroformate (25 g, 0.147 mole). The resulting solution was gradually warmed to room temperature. The stirring was continued at room temperature overnight. The reaction mixture was washed with H2O, dried and purified by flash column chromatography (on silica gel, CH3OH—CH2Cl2) to yield 16.4 g, 58.9% of title compound. 1H NMR (CDCl3): δ 7.26-7.40 (m, 5H), 5.10 & 5.0-5.10 (s+m, 3H), 3.68 (q, 2H), 3.36 (q, 2H), 2.58 (t, 1H), 1.70 (p, 2H).

Source