Methylhydrazine → tert-butyl N-[2-(aminooxy)ethyl]-N-methylcarbamate

Participants

Reaction Steps

To an ice-cold solution of tert-butyl[2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]ethyl]methylcarbamate (4.3 g, 13=mmol) in CH2Cl2/MeOH (8:2, 90 mL) was added methylhydrazine (3.2 mL, 60 mmol) dropwise. The stirred reaction mixture was allowed to warm to ambient temperature. After 1.5 h, the reaction mixture was concentrated under reduced pressure. To the residue was added CH2Cl2 (35 mL) and the resulting white solid was collected by vacuum filtration. The filtrate was concentrated and purified by column chromatography (silica gel, 50:50 hexanes/EtOAc to 35:65 hexanes/EtOAc) to afford tert-butyl[2-(aminooxy)ethyl]methylcarbamate (2.3 g, 90%) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 1.46 (9H, s), 1.82-1.98 (1H, m), 2.88 (3H, br s), 3.44-3.46 (2H, m), 3.74 (2H, t, J=5.3 Hz), 5.44-5.77 (2H, m).

Provenance & Evidence