tert-Butyl 3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate → tert-Butyl 3-(2-oxoethyl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A flask was charged with tert-butyl 3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate (160 g, 623 mmol) and dichloromethane (2,500 ml) and cooled to −78° C. A solution of diisobutylaluminum hydride (800 ml, 1.10 equiv) was added dropwise, such that the internal temperature was maintained at −78° C. After 1 h at 78° C., the reaction mixture was quenched by the addition of 30 ml of methanol. After warming to ambient temperature, the mixture was filtered and the filter cake was washed with dichloromethane (3×1,000 mL). The filtrate was dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether gradient) to afford tert-butyl 3-(2-oxoethyl)pyrrolidine-1-carboxylate as light yellow oil.

Provenance & Evidence