Synthesis
GENERAL STEPS: 4-Amino-1-butanol (0.5 g, 5.61 mmol) was dissolved in acetonitrile (56 mL). The reaction system was cooled to 0 °C, followed by the sequential addition of triethylamine (Et3N, 1.56 mL, 11.22 mmol, 2 equiv) and di-tert-butyl dicarbonate (Boc2O, 1.346 g, 6.17 mmol). The reaction progression was monitored by thin layer chromatography (TLC). After 6.5 h of reaction, the reaction was quenched by the addition of water (20 mL). The reaction mixture was extracted with ethyl acetate (EtOAc, 3 × 30 mL) and saturated saline was added to facilitate phase separation. The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel fast column chromatography (eluent: dichloromethane/methanol, 95:5) to afford 4-(N-tert-butoxycarbonylamino)-1-butanol as a colorless oil (1.06 g, quantitative yield).
References
[1] Organic Letters, 2009, vol. 11, # 9, p. 2019 - 2022
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 6, p. 2536 - 2543
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1151 - 1155
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 191 - 200
[5] Inorganica Chimica Acta, 2016, vol. 452, p. 152 - 158
