N,O-Dimethylhydroxylamine → tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

Participants

Reaction Steps

To a solution of 2-(tert-butoxycarbonylamino)acetic acid (8.75 g, 0.05 mol) in tetrahydrofuran (150 mL) was added CDI (11.34 g, 0.07 mmol) at 0° C. The formed mixture was stirred for 1 h. Then N,O-dimethylhydroxylamine (6.8 g, 0.07 mol) and TEA (8 mL) were added to the above mixture. The mixture was stirred at rt overnight. When the reaction was over, the mixture was concentrated. The residue was washed with 1 N aq HCl and aq. NaHCO3 (3×). The combined organic phase was concentrated to give crude product, which was used for next step without purification. 1H NMR (400 MHz, CDCl3): δ=1.42 (s, 9H), 3.16 (s, 3H), 3.66 (s, 3H), 4.04 (s, 2H), 5.22 (s, 1H).

Provenance & Evidence