Triphenylphosphine → Benzyl 4-{(1R,2S)-2-[2-(4-bromo-2,5 difluorophenoxy)ethyl]cyclopropyl}piperidine-1-carboxylate

Participants

Reaction Steps

Benzyl 4-[(1R,2S)-2-(2-hydroxyethyl)cyclopropyl]piperidine-1-carboxylate (2.24 g, 7.38 mmol) in DCM (35 ml) was added 4-bromo-2,5-difluorophenol (1.62 g, 7.75 mmol), 3.93 g of triphenylphosphine (polymer-bound, 3.0 mmol/g) and di-tert-butyl diazene-1,2-dicarboxylate (2.21 g, 9.60 mmol). The reaction mixture was stirred at RT for 4 hours. The solid was removed by filtration through celite and the filtrate concentrated. The residue was purified by column chromatography on silica gel (Biotage column, 50 g SNAP) using a gradient 0-20% then 20% EtOAc in hexanes to afford the title compound. LC/MS (m/z): 496.2 (M+H)+.

Provenance & Evidence