Potassium Hydroxide → Ethyl 2-(tert-butoxycarbonylaminooxy)propanoate

Participants

Reaction Steps

To a solution of t-butyl hydroxycarbamate (530 mg, 3.98 mmol) and potassium hydroxide (223 mg, 3.98 mmol) in EtOH (10 mL) was added ethyl 2-bromopropanoate (600 mg, 3.31 mmol) slowly at rt. The reaction mixture was heated at reflux overnight. White precipitate was filtered off and the filtrate was concentrated. The resulting residue was dissolved in ether, washed with water and brine, and dried over Na2SO4. Solvent was evaporated to afford the title compound as a clear oil which was used in the next step without further purification (825 mg, 100%). 1H-NMR (400 MHz, CDCl3) δ ppm 7.62 (s, 1H), 4.46 (q, 1H), 4.24 (q, 2H), 1.46 (d, 3H), 1.48 (s, 9H), 1.28 (t, 3H).

Provenance & Evidence