2,2-diphenylpropan-1-amine

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,2-diphenylpropan-1-amine (0.10 g, 0.5 mmol) in dichloromethane (10 mL) under nitrogen was added 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.16 g, 0.50 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.19 g, 1.00 mmol) and N,N-dimethylpyridin-4-amine (6 mg, 0.05 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned in ethyl acetate/water (8:2, 400 mL). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with ethyl acetate/hexane (1:3) gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.05-7.35 (m, 20H), 6.0-6.1 (m, 1H), 3.98 (s, 2H), 3.95 (s, 2H), 3.2-3.4 (m, 2H), 2.4-2.5 (m, 2H), 1.65-1.75 (m, 2H), 1.5 (s, 3H); MS (ESI+) m/z 503 (M+H)+. The reaction was concentrated the residue was partitioned in ethyl acetate/water (8:2, 400 mL) The organic layer was washed with water dried over magnesium sulfate filtered concentrated Silica gel chromatography eluting with ethyl acetate/hexane (1:3)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,2-diphenylpropan-1-amine (0.21 g, 1.00 mmol) in dichloromethane (25 mL) under nitrogen was added 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (Example 58D, 0.33 g, 1.00 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.39 g, 2.00 mmol) and N,N-dimethylpyridin-4-amine (0.012 g, 0.10 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned in ethyl acetate/water (8:2). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with 3% methanol/dichloromethane gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.10-7.29 (m, 14H), 6.94-7.01 (m, 4H), 5.66 (t, J=5.4 Hz, 1H), 3.95 (d, J=5.8 Hz, 2H), 3.89 (s, 2H), 3.27 (t, J=6.4 Hz, 2H), 2.55 (t, J=6.4 Hz, 2H), 1.59 (s, 3H); MS (DCI+) m/z 525 (M+H)+. The reaction was concentrated the residue was partitioned in ethyl acetate/water (8:2) The organic layer was washed with water dried over magnesium sulfate filtered concentrated Silica gel chromatography eluting with 3% methanol/dichloromethane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,2-diphenylpropan-1-amine (0.21 g, 1.00 mmol) in dichloromethane (20 mL) under nitrogen was added 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.30 g, 1.00 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.38 g, 2.00 mmol) and N,N-dimethylpyridin-4-amine (0.61 mg, 0.005 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned in ethyl acetate/water (8:2, 400 mL). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography eluting with ethyl acetate/hexane (1:1) gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.09-7.33 (m, 20H), 5.72-5.77 (m, 1H), 3.95 (d, J=5.9 Hz, 2H), 3.91 (s, 2H), 3.23 (t, J=6.4 Hz, 2H), 2.58 (t, J=6.4 Hz, 2H), 1.57 (s, 3H); MS (DCI+) m/z 489 (M+H)+. The reaction was concentrated the residue was partitioned in ethyl acetate/water (8:2, 400 mL) The organic layer was washed with water dried over magnesium sulfate filtered concentrated Silica gel chromatography eluting with ethyl acetate/hexane (1:1)