Water → N-Methoxy-N-methyl-3-cyclopentenecarboxamide

To a solution of cyclopent-3-ene-1-carboxylic acid (80.0 g, 0.71 mol) in dichloromethane (300 ml) was added 1,1′-carbonyldiimidazole (127.5 g, 0.78 mol) slowly and the reaction mixture was stirred at room temperature for 1 h. N,O-dimethylhydroxylamine (76.7 g, 0.78 mol) was added and stirred for 18 h at room temperature. The reaction mixture was poured into water (300 ml) and extracted with dichloromethane (100 ml). The organic extracts were washed with hydrochloric acid (1N, 2×200 ml) and then with brine before filtering through cotton wool, drying and concentrating. The product was purified by flash chromatography using silica gel eluting with dichloromethane to give the title compound (116.78 g, 95%).

1. stirringstirred for 18 h at room temperature
2. extractionextracted with dichloromethane (100 ml)
3. washThe organic extracts were washed with hydrochloric acid (1N, 2×200 ml)
4. filtrationwith brine before filtering through cotton wool
5. customdrying
6. concentrationconcentrating
7. customThe product was purified by flash chromatography

ORD record

ord-4c91d00ada6544f89d75bc2a969914fe

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07494992B2