3-Amino-1-propanol → tert-butyl N-(3-hydroxypropyl)carbamate

Participants

Reaction Steps

A solution of 3-aminopropanol (15 mL, 0.20 mol) in methylene chloride (50 mL) at rt was treated with t-butylpyrocarbonate (42.02 g, 1 equiv) in methylene chloride (25 mL), dropwise over 2 h. After stirring overnight the mixture was evaporated, flushed with heptane (3×), and dried in vacuo to give the product as a thick oil (34.31 g, 100%). 1H NMR δ 1.48 (s, 9H), 3.12 (br, 1H), 3.22 (q, J=7.5 Hz, 2H), 3.60 (q, J=7.8 Hz, 2H), 4.81 (br, 1H). MS (DCl) 176 (MH)+. Anal calcd for C8H17NO3: C-54.84, H-9.78, N-7.99. Found: C-54.80, H-9.82, N-7.97.

Provenance & Evidence