tert-butyl N-(3-methoxypropyl)carbamate

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of carbamate 270 (5.0 g, 26.4 mmol), crushed KOH (3.8 g, 67.7 mmol) in MeI (15 mL) was stirred at 20° C. for 72 h under N2. The solution was filtered through Celite, washed with DCM (2×50 mL) and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (30-50%) of EtOAc/pet. ether, to give carbamate 271 (2.0 g, 37%) as a colourless oil: 1H NMR δ 3.38 (t, J=6.3 Hz, 2H, CH2N), 3.33 (s, 3H, OCH3), 3.28 (t, J=7.0 Hz, 2H, CH2O), 2.85 (s, 3H, NCH3), 1.78 (tt, J=7.0, 6.3 Hz, 2H, CH2), 1.46 [s, 9H, C(CH3)3]; MS (APCI) m/z 104 (MH+-tBuCO2, 100%); HRMS (FAB+) calcd for C10H22NO3 (MH+) m/z 204.1600, found 204.1605. The solution was filtered through Celite washed with DCM (2×50 mL) the solvent evaporated The residue was purified by chromatography eluting with a gradient (30-50%) of EtOAc/pet. ether