Ammonia → (3R,4S)-3,4-dimethylpyrrolidine-2,5-dione

Participants

Reaction Conditions

Reaction Steps

In a cooling bath, ammonia gas was introduced into a toluene (5 ml) solution of 390 mg of cis-2,3-dimethylsuccinic anhydride for 30 minutes. The solvent was evaporated away under reduced pressure to obtain a white solid. This was dissolved in 10 ml of DMF, and at −78° C., 0.5 ml of thionyl chloride was added to it and stirred at 0° C. for 2 hours. The reaction liquid was restored to room temperature, the solvent was evaporated away under reduced pressure, ethyl acetate was added to the residue, and washed with aqueous saturated sodium hydrogencarbonate solution. After dried, the solvent was removed, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=7/3 to 0/1) to obtain 269 mg of the entitled compound as a white solid.

Provenance & Evidence