Hydrochloric Acid → HCID 57425668, compound

Participants

Reaction Conditions

Reaction Steps

N,O-Dimethylhydroxylamine hydrochloride (1.66 g, 17.0 mmol) was suspended in 20 mL of dry TVF and cooled to 0° C. Trimethylaluminum (8.50 mL, 2.0M solution in toluene, 17.0 mmol) was added slowly and stirred for 30 minutes. Methyl morpholin-4-yl-(phenyl)acetate (1.00 g, 4.25 mmol) was added to the cooled mixture in an 8 mL TIFF solution. The reaction was allowed to warm to ambient temperature while for 18 hours. The mixture was poured into 1N HCl(aq) and stirred for 1 hour. The mixture was then poured into NaHCO3(sat) and extracted 3× with EtOAc. The combined organic layers were washed 1× with brine, dried with Na2SO4, filtered and concentrated in vacuo to provide N-methoxy-N-methyl-2-morpholin-4-yl-2-phenylacetamide. HRMS [M+H] C14H21N2O3 calc'd 265.1547. found 265.1553.

Provenance & Evidence