Ethanolamine → Tert-butyl 3-{[(benzyloxy)carbonyl](2-hydroxyethyl)amino}propanoate

Participants

Reaction Steps

6.11 g (100 mmol) of ethanolamine were cooled (0° C.), treated with 14.52 ml (100 mmol) of ter-butyl-acrylate and stirred 15 min at this temperature. During warming up to room temperature the reaction started and was kept with cooling at 25-30° C. and then stirred 18 h at room temperature. The oil was dissolved in 500 ml of tetrahydrofuran and 500 ml of water, 27.42 (110 mmol) of N-(benzyloxycarbonyloxy)succinimide were added at 0° C. followed by 27.88 ml (200 mmol) of triethlamine. The reaction was stirred at room temperature over 3 h, then partitioned between 10% aq. potassium hydrogensulfate solution and diethyl ether (3×). The organic phases were washed with 10% aq. potassium hydrogensulfate solution, sat. aq. sodium hydrogencarbonate solution, 10% aq. sodium chloride solution, dried over Na2SO4 evaporated and purified by flash silica gel column (n-heptane/ethyl acetate 4:1 to 1:1) to yield 27.53 g (85%) of the title compound as light yellow oil. MS: 324.2 (MH+).

Provenance & Evidence