Into a 100 mL round-bottom flask were placed tert-butyl (3- hydroxypropyl)(methyl)carbamate (2.00 g, 10.60 mmol, 1.00 equiv), DCM (20.00 mL) and PPh3 (3.67 g, 13.80 mmol, 1.30 equiv). This was followed by addition of CBr4 (5.20 g, 13.80 mmol, 1.30 equiv) at 0 °C. The resulting solution was stirred for 1.5 h at 0 °C. The reaction mixture was quenched with H2O (50.00 mL), extracted with DCM (100 mL*2). The combined organic phase was washed with Na2CO3 (aq), brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column with petroleum ether/ethyl acetate (93%/7%). This resulted in 2.6 g of 3-Bromo-N-methyl-N-boc-propylamine as light yellow oil.
