Synthesis
General procedure for the synthesis of tert-butyl 4-(bromomethyl)benzylcarbamate from tert-butyl 4-(hydroxymethyl)benzylcarbamate: 4-(N-tert-butoxycarbonylaminomethyl)benzyl alcohol (250 mg, 1.1 mmol) was dissolved in tetrahydrofuran (5 mL) and cooled down to -78 °C. At this temperature, phosphorotriamine (30 μL, 0.32 mmol) was slowly added and the reaction lasted for 2 hours. Upon completion of the reaction, solid sodium bicarbonate (50 mg) was added to quench the reaction. The solid insoluble material was removed by filtration and the filtrate was subsequently evaporated to afford the target product 4-(tert-butoxycarbonylaminomethyl)benzyl bromide (300 mg, 95% yield).
References
[1] Patent: US6680311, 2004, B1. Location in patent: Page/Page column 151
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 1, p. 33 - 47
[3] Patent: WO2006/117549, 2006, A1. Location in patent: Page/Page column 155
[4] Chemical Science, 2017, vol. 8, # 12, p. 7947 - 7953
