Methylamine → N-(2-Ethoxycarbonyl-ethyl)-N-methyl-malonamic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) solution of methylamine in ethanol (400 mL; 33% wt), ethyl acrylate (39.7 g, 0.397 mol) was added over a period of 20 minutes. The reaction mixture was stirred at 0° C. for 2 hours, and concentrated under vacuum. The crude product was used without further purification. The above crude product (21.8 g, 0.166 mol), diisopropylethylamine (28.9 mL, 0.166 mol), and 4-(N,N-dimethylamino)pyridine (2 g, 16 mmol) was dissolved in dichloromethane (300 mL) and cooled to 0° C. The mixture was treated with ethyl 3-chloro-3-oxopropionate (21.3 mL, 0.166 mol) and stirred at 0° C. for one hour. The mixture was allowed to warm up to room temperature and stirred overnight. The reaction mixture was partitioned with aq HCl (400 mL, 1M). The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide the title compound as yellow oil

Provenance & Evidence