Synthesis
The general procedure for the synthesis of tert-butyl (2-hydroxyethyl)carbamate from di-tert-butyl dicarbonate and N-ethyl ethanolamine was as follows: to a mixed solution containing 2-(ethylamino)ethanol (8.91 g) and ethyl acetate (100 mL) was added di-tert-butyl dicarbonate (21.8 g) slowly under ice-bath cooling conditions. The reaction mixture was stirred continuously at room temperature for 3 days. Upon completion of the reaction, the mixture was washed with saturated brine (100 mL) and the organic phase was subsequently dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give the title compound (19.0 g) as a colorless oil. The product was characterized by 1H-NMR (CDCl3): δ 1.11 (3H, t, J = 7.0 Hz), 1.47 (9H, s), 3.27 (2H, q, J = 7.0 Hz), 3.37 (2H, t, J = 5.2 Hz), 3.73 (2H, q, J = 5.2 Hz).
References
[1] Synthetic Communications, 1993, vol. 23, # 17, p. 2443 - 2449
[2] Chemical Communications, 2015, vol. 51, # 49, p. 9987 - 9990
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 6, p. 1547 - 1551
[4] Journal of the American Chemical Society, 2002, vol. 124, # 41, p. 12182 - 12191
[5] Patent: WO2005/80343, 2005, A2. Location in patent: Page/Page column 51-52
