1-[4-(Bromomethyl)phenyl]-1H-pyrrole → HCID 54243183, compound

Participants

Reaction Steps

To a -78° C. solution of lithium bis(trimethylsilylamide (8 mL, 8 mmol) in THF is slowly added N-(3,5-dimethylbenzoyl)proline methyl ester (1.0 g, 3.8 mmol). After 20 minutes p-(1-pyrrolyl)-benzyl bromide (950 mg) in 5 mL of THF is added over a 5 minute period. The solution is warmed to room temperature, quenched with acetic acid and concentrated under reduced pressure. The residue is extracted with EtOAc. The organic layer is washed with NH4Cl (sat.), NaHCO3 solution, dried (MgSO4) and chromatographed on silica gel eluting with hexane/ethyl acetate (3:1) giving N-(3,5-dimethylbenzoyl)-2-[p-(1-pyrrolyl)-benzyl]-proline methyl ester.

Provenance & Evidence