N,N-Dimethylaniline → HCID 15927742, compound

Participants

Reaction Conditions

Reaction Steps

Cyclobutanol (2 g, 27.7 mmol) and N,N-Dimethylaniline (3.69 g, 30.5 mmol) were slowly added to a mixture of triphosgene (8.22 g, 27.7 mmol, 1 eq) in dry THF (20 mL) at 0° C. After 10 minutes, the reaction was warmed to 10° C. and stirred for 12 hour. Dry CH2Cl2 (20 mL) was added and the mixture was poured slowly into a solution of N-hydroxysuccinimide (4.14 g, 36 mmol) in dry CH2Cl2 (20 mL) at 0° C. The mixture was stirred at 10° C. for 10 hours. H2O (20 mL) was added and the mixture was stirred for 3 hours. The mixture was extracted with ethyl acetate (2×30 mL). The organic layer was washed with brine (20 mL) and dried over Na2SO4. The solvent was removed under vacuum resulting in cyclobutyl 2,5-dioxopyrrolidin-1-yl carbonate (1 g, 16% yield).

Provenance & Evidence