Dimethyl Sulfoxide → Tert-butyl 3-oxopyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Dimethylsulfoxide (DMSO; 1.56 ml; 22 mmol) was added over 15 minutes to a solution of oxalyl chloride (0.97 ml; 11 mmol) in CH2Cl2 (20 ml) at -60° C. After stirring 15 minutes at -60° C., the title compound of Step (A) (1.87 g; 10 mmol) was added dropwise over 15 minutes as a solution in CH2Cl2 (20 ml). After stirring 15 minutes at -60° C., diisopropylethylamine (8.75 ml; 50 mmol) was added over 5 minutes. After stirring 15 minutes at -60° C., the reaction mixture was allowed to warm to room temperature and stir 30 minutes. The reaction mixture was diluted with CH2Cl2 (100 ml) and was washed with saturated KHSO4 solution (2×100 ml), saturated NaHCO3 solution (100 ml) and brine (100 ml). Drying (MgSO4) and concentration afforded 1.87 g (99%) of the title compound of this step as a light yellow oil.

Provenance & Evidence