4-Methylmorpholine → 1-{[3-(2-Methyl-1,3-dioxolan-2-yl)propanoyl]oxy}pyrrolidine-2,5-dione

Participants

Reaction Steps

A solution of 3-(2-methyl-1,3-dioxolan-2-yl)propanoic acid (8.95 g, 55.9 mmol) in dichloromethane (111 mL) was cooled to approximately 0° C. N-hydroxysuccinimide (7.10 g, 61.5 mmol), 4-methylmorpholine (6.22 g, 61.5 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (11.8 g, 61.5 mmol) were sequentially added with stirring. The reaction was then allowed to warm to room temperature, stirred for 17 hours, and partitioned between dichloromethane (150 mL) and water (50 mL). The organic layer was separated; sequentially washed with water (50 mL), saturated aqueous sodium bicarbonate (2×50 μL), and brine (50 mL); dried over sodium sulfate; filtered; and concentrated under reduced pressure to provide 13 g of 1-{[3-(2-methyl-1,3-dioxolan-2-yl)propanoyl]oxy}pyrrolidine-2,5-dione as a white solid.

Provenance & Evidence