4-Methylmorpholine → 1,1-Dimethylethyl [4-(methoxymethylamino)-4-oxobutyl]-carbamate

Participants

Reaction Steps

4-(Dimethylamino)pyridine (6.11 g), N,O-dimethylhydroxylamine hydrochloride(4.88 g), N-methylmorpholine (5.06 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (9.58 g) were added in quick succession to a solution of 4-(tert-butoxycarbonylamino)butyric acid (10.16 g) in dichloromethane (200 ml). The reaction mixture was then stirred under ambient conditions for 18 h. The solution was then washed with 2M hydrochloric acid solution, 10% sodium bicarbonate solution and brine. The organic layer was separated, dried over magnesium sulfate, filtered and the filtrate evaporated to dryness to give the subtitle compound as a colourless oil (10.2 g, 83%).

Provenance & Evidence