Methylamine → Benzyl (2-(aminooxy)ethyl)carbamate

Participants

Reaction Steps

To a solution of N-[2-(benzyloxycarbonylamino)ethoxy]phthalimide (1.36 g, 4.00 mmol), as prepared in the preceding step, in ethanol (20 mL) and tetrahydrofuran (20 mL) was added 40% methylamine (2.0 mL, 25 mmol) and the reaction was stirred at ambient temperature for 1 h. After evaporating the solvent, the residue was purified by flash column chromatography (75-100% ethyl acetate in hexanes) to give the title compound as a white solid (0.80 g, 95%). 1H-NMR (300 MHz, CDCl3) δ 7.36 (m, 5H), 5.47 (bs, 2H), 5.21 (bs, 1H), 5.10 (s, 2H), 3.72 (t, J=5.0 Hz, 2H), 3.44 (q, J=5.0 Hz, 2H).

Provenance & Evidence