Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

Participants

Reaction Steps

The procedure is generally as depicted in FIG. 16. Dissolve 6.1 g (10 mmol) of ethanolamine in 10 mL of 1N NaOH. Cool the solution with an ice bath and add to it a solution of 1.7 g (10 mmol) of benzyl chloroformate dissolved in 10 mL of 1,4-dioxane, dropwise, over a period of 30 minutes. When the addition is complete, remove the ice bath and stir for 30 minutes. Add 100 mL of ethyl acetate and wash with 3×50 mL of 1.0N HCl. Wash the ethyl acetate layer with 50 mL of brine. Dry the ethyl acetate layer over anhydrous sodium sulfate. Filter and concentrate the filtrate to a residue. Final purification is achieved by flash chromatography on silica gel with ethyl acetate/hexane as the eluent. N-Cbz-ethanolamine, compound 52, is isolated as an oil.

Provenance & Evidence