Methylhydrazine → (S)-O-(2-((tert-Butyldimethylsilyl)oxy)propyl)hydroxylamine

Participants

Reaction Conditions

Reaction Steps

To a cold solution of crude 2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-propoxy]-isoindole-1,3-dione (0.28 mol) in DCM (200 ml) at 0° C. was added methyl hydrazine (14.74 mol, 0.28 mol). The reaction mixture was stirred at 0° C. for 30 minutes then filtered and the filtrate concentrated in vacuo. The resultant residue was subjected to distillation (b.p. 108-112° C. at 2-10 mbar) to yield the title compound as a colourless oil. (42.63 g, 74% from ethyl lactate). 1H NMR (CDCl3, 400 MHz) 5.36 (2H, s), 3.95 (1H, m), 3.55-3.41 (2H, m), 1.04 (3H, d, J=6.28 Hz), 0.81 (9H, s), 0.02 (6H, m).

Provenance & Evidence