Benzyl 4-{(1R,2S)-2-[2-(4-bromo-2,5 difluorophenoxy)ethyl]cyclopropyl}piperidine-1-carboxylate (0.540 g, 1.09 mmol) in THF (5 ml) was added 0.5 M 2-tert-butoxy-2-oxoethylzinc chloride in diethyl ether (5.46 ml, 2.73 mmol), followed by Pd2(dba)3 (50 mg, 0.055 mmol) and 52 mg X-Phos. The vessel was evacuated and back filled with nitrogen (3×) and the mixture was heated at 65° C. overnight. Saturated ammonium chloride (10 ml) was added and the mixture extracted with EtOAc (15 ml). The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by column chromatography on silica gel (Biotage SNAP column, 25 g) using a gradient 0-15% then 15% EtOAc in hexanes to afford the title compound. LC/MS (m/z): 552.4 (M+Na)+.
