Synthesis
General procedure for the synthesis of tert-butyl benzyl (2-hydroxyethyl) carbamate from di-tert-butyl dicarbonate and N-benzylethanolamine: a solution of di-tert-butyl dicarbonate (0.01 mol) in dichloromethane (15 mL) was added slowly and dropwise to a mixture containing 2-benzylaminoethanol (0.01 mol), dichloromethane (15 mL), and a 1 M aqueous sodium hydroxide solution (12 mL). . The reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the organic layer was separated, washed sequentially with water (25 mL × 2) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product as an oil. The crude product was purified by silica gel column chromatography with the eluent of petroleum ether: ethyl acetate (7:3, v/v) to obtain the target product tert-butyl benzyl (2-hydroxyethyl)carbamate in 100% yield.
References
[1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 3, p. 295 - 300
[2] Journal of Organic Chemistry, 2000, vol. 65, # 20, p. 6368 - 6380
[3] Patent: WO2005/26111, 2005, A2. Location in patent: Page/Page column 17
[4] Patent: WO2008/42353, 2008, A1. Location in patent: Page/Page column 19; 21
[5] Patent: TW2016/2105, 2016, A. Location in patent: Paragraph 0563
