Synthesis
The general procedure for the synthesis of tert-butyl (3-amino-2-hydroxypropyl)carbamate from di-tert-butyl dicarbonate and 1,3-diamino-2-propanol was as follows: 0.9 g of 1,3-diamino-2-propanol was added to a reactor equipped with magnetic stirring, and dissolved with 5 mL of 1 M sodium hydroxide solution. Subsequently, 1.0 g of di-tert-butyl dicarbonate was dissolved in 5 mL of 1,4-dioxane and this solution was slowly added dropwise to the reactor. The reaction mixture was stirred at room temperature for 5 hours and then warmed up to 50-65 °C for decompression distillation to remove most of the solvent, and the remaining solvent was dried by a vacuum pump to give a white viscous solid. The crude product was purified by silica gel column chromatography with gradient elution using dichloromethane-methanol-triethylamine (300:30:1, v/v/v) as eluent to give 600 mg of tert-butyl (3-amino-2-hydroxypropyl)carbamate in 69% yield.
References
[1] Patent: CN106893342, 2017, A. Location in patent: Paragraph 0016; 0017
[2] Patent: CN105503920, 2016, A. Location in patent: Paragraph 0011; 0057; 0058
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 2, p. 236 - 246
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 46, p. 9389 - 9404
[5] Patent: WO2005/66172, 2005, A1. Location in patent: Page/Page column 62
