Imidazole → HCID 58218809, compound

Participants

Reaction Conditions

Reaction Steps

Imidazole (261.5 mg, 3.84 mmol), triphenylphosphine (670.7 mg, 2.56 mmol) and I2 (487.3 mg, 1.92 mmol) were added sequentially to a solution of 1-(2,6-dimethylphenyl)-3-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (prepared from step c, 373 mg, 1.28 mmol) in toluene (15 mL) and resulting reaction mixture was heated at 100° C. with stirring for an hour. The reaction mixture was then cooled to room temperature and diluted with EtOAc (50 mL), washed with water (30 mL), saturated NH4Cl (30 mL), dried (Na2SO4) and evaporated. The residue was then purified by flash chromatography (SiO2, 20→70% EtOAc/hexanes) to obtain 1-(2,6-dimethylphenyl)-3-iodomethyl-4-methyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (427 mg, 83% yield). LC-MS: Rt (retention time): 2.32 min, MS: (ES) m/z 402.2 (M+H+).

Provenance & Evidence