Bromobenzene → Methyl 5-oxo-1-phenylprolinate

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-oxo-pyrrolidine-2-carboxylic acid methyl ester (5.00 g, 34.9 mmol), bromobenzene (5.48 g, 34.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.96 g, 1.05 mmol), Xantphos™ (1.21 g, 2.09 mmol), and cecium carbonate (15.9 g, 48.9 mmol) in toluene (100 mL) was stirred at 120° C. for 20 h under argon atmosphere. The reaction mixture was cooled to room temperature, and partitioned between ethyl acetate and 2 M HCl solution. The organic layer was washed with saturated NaHCO3 solution, and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 70:30 to 0:100) to give a yellow solid. The solid was triturated with hexane-diisopropyl ether to give the title compound (3.74 g, 49%) as a yellow solid.

Provenance & Evidence