Dichloromethane → 2-cyclopropyl-N-methoxy-N-methylacetamide

A 500 mL round bottom flask was charged with cyclopropylacetic acid (9.87 g, 98.6 mmol) (available from Oakwood) and DCM (200 mL). To the stirred solution was added 1,1′-carbonyldiimidazole (19.2 g, 118 mmol) portionwise (vigorous gas evolution). The yellow solution was stirred for 30 minutes at room temperature, and to it was added N,O-dimethylhydroxylamine hydrochloride (11.5 g, 118 mmol) (available from Aldrich) in one portion. The heterogeneous, white mixture was stirred overnight and diluted with ether (300 mL). The organics were washed with 1 N HCl (2×150 mL), saturated aqueous NaHCO3 (2×150 mL) and brine (1×150 mL), dried (MgSO4), and concentrated to afford 84.B (11.9 g, 84.3% yield) as a colorless liquid. The crude product was used without further purification.

1. stirringThe heterogeneous, white mixture was stirred overnight
2. washThe organics were washed with 1 N HCl (2×150 mL), saturated aqueous NaHCO3 (2×150 mL) and brine (1×150 mL)
3. dry with materialdried (MgSO4)
4. concentrationconcentrated

ORD record

ord-b06691af69654b89b8564831e348a6a4

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030354B2