Allyl bromide → 1-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(allyl)-2-oxopyrrolidine

Participants

Reaction Conditions

Reaction Steps

Combine 1-(3,4,5-trimethoxybenzyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine (0.93 g, 2.86 mmol) and tetrahydrofuran (10 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of sec-butyl lithium (2.64 mL, 1.3 M in hexane, 3.43 mmol). After 30 minutes, add allyl bromide (0.42 g, 3.43 mmol). After the addition is complete, warm to ambient temperature. After 3 hours, add water and extract three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with ethyl acetate/hexane 1/4 to give the title compound.

Provenance & Evidence