To a solution of tert-butyl 6-chloro-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (310 mg, 1.096 mmol), prepared as described in Example 19A, in 1,2-dichloroethane (7 mL) was added benzaldehyde (235 mg, 2.193 mmol), followed by sodium triacetoxyborohydride (650 mg, 3.069 mmol) and AcOH (200 mg, 3.29 mmol). The reaction mixture was stirred at RT for 4 h, then diluted with EtOAc, washed with saturated aqueous NaHCO3, water, saturated aqueous NaCl, dried Na2SO4) and concentrated. The resulting residue was chromatographed (silica gel) eluting with EtOAc/hexanes (1:5 ratio) to give the title compound as light yellow foam (325 mg, 80%).
