2-Bromobenzyl alcohol → HCID 68555942, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2-bromophenyl)methanol (56 g) in tetrahydrofuran (300 mL) was cooled to −78° C., n-butyllithium (1.6 M, hexane solution, 390 mL) was slowly added dropwise. After stirring at −78° C. for 1 hr, a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (60 g) in tetrahydrofuran (200 mL) was added dropwise. The reaction mixture was warmed to room temperature, and the mixture was stirred at room temperature overnight. The reaction was quenched with water and stirring at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, and washed with aqueous sodium chloride solution. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate, 40%-80%) and crystallized from ethyl acetate-hexane to give the object product (35 g).

Provenance & Evidence