Benzyl Bromide → 1-Benzyl 2-methyl (2S)-pyrrolidine-1,2-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

To a tetrahydrofuran solution (1 ml) of the compound prepared in Example 7 (146 mg), were successively added dropwise at 0° C. in a nitrogen atmosphere benzyl bromide (0.114 ml, 0.96 mmol) and a tetrahydrofuran solution of tetrabutyl ammonium fluoride (0.48 ml, 0.48 mmol). The mixture was stirred for 1 hour at 0° C., poured into water and extracted with ether. The ether layer was dried over anhydrous magnesium sulfate and concentrated under vacuum. The resulting reaction mixture was subjected to column chromatography on silica gel and eluted with a 1:1 mixture of ether and hexane to give the titled compound in an amount of 94 mg (yield, 75% based on the starting materials used in Example 7).

Provenance & Evidence