tert-butyl N-(2-phenylphenyl)carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl[1,1′-biphenyl]-2-ylcarbamate (synthesized according to Tsang et al., J. Org. Chem., 7603 (2008)) (12.5 g, 46.4 mmol) in diethyl ether (125 mL) at −30° C. was added tert-butyllithium (1.6 M in pentane, 174 mL, 278 mmol) slowly over 15 minutes. The reaction mixture was stirred for 6 h, then a solution of perchloroethane (43.9 g, 186 mmol) in diethyl ether (125 mL) was added over 10 minutes. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride and extracted twice with EtOAc. The organic layers were washed with brine, dried with sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (EtOAc/petroleum ether) to give Preparation 8A (8.5 g, 60%). HPLC: RT=2.432 min (H2O/MeCN with TFA, SunFire C18 3.5 μm, 4.6×150 mm, gradient=30 min, wavelength=220 and 254 nm). stirred overnight The reaction was quenched with saturated aqueous ammonium chloride extracted twice with EtOAc The organic layers were washed with brine dried with sodium sulfate concentrated The residue was purified by silica gel chromatography (EtOAc/petroleum ether) to give

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl[1,1′-biphenyl]-2-ylcarbamate (synthesized according to Tsang et al., J. Org. Chem., 7603 (2008)) (12.5 g, 46.4 mmol) in diethyl ether (125 mL) at −30° C. was added tert-butyllithium (1.6 M in pentane, 174 mL, 278 mmol) slowly over 15 minutes. The reaction mixture was stirred for 6 h, then a solution of perchloroethane (43.9 g, 186 mmol) in diethyl ether (125 mL) was added over 10 minutes. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride and extracted twice with EtOAc. The organic layers were washed with brine, dried with sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (EtOAc/petroleum ether) to give Preparation 8A (8.5 g, 60%). HPLC: RT=2.432 min (H2O/MeCN with TFA, SunFire C18 3.5 μm, 4.6×150 mm, gradient=30 min, wavelength=220 and 254 nm). stirred overnight The reaction was quenched with saturated aqueous ammonium chloride extracted twice with EtOAc The organic layers were washed with brine dried with sodium sulfate concentrated The residue was purified by silica gel chromatography (EtOAc/petroleum ether) to give