Dichloromethane → Methyl 3-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate

Participants

Reaction Steps

To a solution of tert-butyl 1-(3-bromophenyl)ethylcarbamate (300 mg, 1 mmol) in methanol (10 mL) was added [1,1′-bis(diphenyl-phosphino)ferrocene]palladium [II]chloride, 1:1 complex with dichloromethane (146 mg, 0.2 mmol) then triethylamine (0.28 mL, 2 mmol). The mixture was evacuated and backfilled with carbon monoxide four times and was then heated to reflux and stirred under an atmosphere of carbon monoxide for 17 hours. After this time the mixture was filtered through Celite to give a brown solid which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give methyl 3-{1-[(tert-butoxycarbonyl)amino]ethyl}benzoate (210 mg, 75%) as a white solid.

Provenance & Evidence