Triethylamine → 1-(4-Bromophenethyl)pyrrolidine

Participants

Reaction Steps

A solution of 4-bromophenethyl 4-methylbenzenesulfonate (500 mg, 1.407 mmol) from Example 56A in anhydrous acetonitrile (3 mL) was treated with triethylamine (0.589 mL, 4.22 mmol) and pyrrolidine (0.349 mL, 4.22 mmol). The reaction was stirred 16 hours at ambient temperature. The reaction was diluted with ethyl acetate and washed with water, saturated ammonium chloride, and brine. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 5% methanol in dichloromethane, to give the title compound. MS DCI(+) m/z 254.0 [M+H]+.

Provenance & Evidence