Tetrahydrofuran → 1-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine

Participants

Reaction Conditions

Reaction Steps

Combine 1-(3,4,5-trimethoxybenzyl)-2-oxopyrrolidine (0.98 g, 3.70 mmol) and tetrahydrofuran (10 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of sec-butyl lithium (2.99 mL, 1.3 M in hexane, 3.88 mmol). After 30 minutes, add 4-fluorobenzyl bromide (0.70 g, 3.70 mmol). After the addition is complete, warm to ambient temperature. After 2 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 1/1 to give the title compound.

Provenance & Evidence