Benzyl Bromide → (S)-(+)-1-Benzyl-5-ethoxycarbonylpyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

Ethyl (S)-(+)-2-pyrrolidone-5-carboxylate (1 g, 6.36 mmol) and benzyl bromide (0.76 mL, 6.36 mmol) were placed in dry THF (30 mL). The reaction mixture was stirred and cooled to 0° C. A 1M solution of tert-BuOK was added dropwise (6.36 ML, 6.36 mmol) and the reaction was stirred for an additional 0.5 h at 0° C. and allowed to come to room temperate where it was stirred for 24 hours under N2. The reaction was then dissolved into a 1:1 mixture of H2O/EtOAc. The organic layer was washed with 1M HCl, H2O and brine, and then dried over MgSO4 to afford N-benzyl-L-pyroglutamic acid ethyl ester an oil.

Provenance & Evidence