Hydrochloric Acid → N-Methoxy-N-methyl-3-(2-ethylbutyl)cyclobutanecarboxamide

Participants

Reaction Steps

3-(2-Ethylbutyl)cyclobutanecarboxylic acid (10.0 g) and chloroform (100 mL) were mixed. To the mixture were added N,O-dimethylhydroxylamine hydrochloride (6.36 g), N,N-diisopropylethylamine (11.3 mL), WSC.HCl (12.5 g) and 4-dimethylaminopyridine (7.96 g) at ice temperature. The mixture was stirred at RT overnight. After an addition of 6 N hydrochloric acid (40 mL) at ice temperature, the aqueous layer was removed. The organic layer was washed with 1 N hydrochloric acid (50 mL), water (50 mL), saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (13.2 g) as a crude product.

Provenance & Evidence