Reaction Steps
To a solution of 2-(4-chlorophenoxy)phenylamine (130 mg, 0.51 mmol), N-(ethoxycarbonyl)-tropinone (201 mg, 1.02 mmol) and acetic acid (153 mg, 2.55 mmol) in DCE (4 ml), was added sodium triacetoxyborohydride (270 mg, 1.28 mmol). The reaction mixture was allowed to stir at room temperature for 10 days. On return, the reaction was quenched with saturated aqueous sodium sodium bicarbonateonate (15 ml) and extracted with ethyl acetate (2×15 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography then proceeded (eluent; 9:1 hexane:ethyl acetate to ethyl acetate) to afford the title compound as a pale yellow oil (49.7 mg, 22%). 1H NMR (270 MHz, CDCl3): δ 1.24 (3H, t, J=7.2 Hz, CH3), 1.63-1.86 (6H, m, 2×CH2, 2×CH), 2.03-2.18 (2H, m, 2×CH), 3.69-3.72 (1H, m, CH), 4.05-4.30 (3H, m, CH2, NH), 4.39 (1H, d, J=4.5 Hz, CH), 6.57-6.68 (2H, m, Ar—H), 6.77 (1H, d, J=8.9 Hz, Ar—H), 6.82-6.86 (1H, dd, J=1.5, 7.9 Hz, Ar—H), 7.04-7.07 (1H, d, J=1.5, 7.5 Hz, Ar—H), 7.09-7.13 (1H, dd, J=2.2, 8.8 Hz, Ar—H), 7.44-7.45 ppm (1H, d, J=2.5 Hz, Ar—H). 13C NMR (67.93 MHz, CDCl3): δ 14.9, 28.0, 28.3, 35.0, 35.6, 44.5, 52.4, 61.0, 111.5, 116.8, 118.1, 120.1, 125.9, 128.0, 130.3, 132.0, 138.9, 142.0, 152.0, 153.9 ppm. LCMS: M+H, 435.44 HPLC: 95.62% (5.044 min, isocratic 90% acetonitrile, 10% water at 1 ml/min).
