反应详情

温度

60 °C

To a suspension of 4-Hydroxy-6-methoxy-1-methyl-1H-quinolin-2-one (1.8 g, 10 mmol) in DMF (30 mL) was added sodium hydride (385 mg, 10 mmol, 60% dispersion in mineral oil). After stirring for 5 minutes, N-phenyltrifluoromethanesulfonamide (3.4 g, 10 mmol) was added and the reaction was stirred and monitored by TLC to completion (20 minutes). 4-amino-piperidine-1-carboxylic acid ethyl ester was then added and the reaction mixture was heated at 60° C. over night. The reaction mixture was then diluted up with EtOAc and washed with water, NaHCO3, and brine. The organic portion was dried over MgSO4 and evaporated to afford a residue which was purified by flash chromatography through a silica gel column with dichloromethane and methanol (95:5 v/v) to provide the title compound (445 mg, 12%). 1H NMR (300 MHz, CDCl3) δ 1.27 (2H, t, J=7.11 Hz), 1.22-1.35 (2H, m), 1.40-1.55 (2H, m), 2.10-2.20 (2H, m), 2.90-3.05 (2H, m), 3.50-3.70 (1H, m), 3.64 (3H, s), 3.87 (3H, s), 4.14 (2H, q, J=7.10), 4.50 (1H, br d, J=7.3 Hz), 5.29 (1H, s), 6.95 (1H, d; J=2.31 Hz), 7.17 (1H, dd, J=2.31, 9.03 Hz), 7.30 (1H, d, J=8.94 Hz).

1. stirringthe reaction was stirred
2. custommonitored by TLC to completion (20 minutes)
3. washwashed with water, NaHCO3, and brine
4. dry with materialThe organic portion was dried over MgSO4
5. customevaporated
6. customto afford a residue which
7. customwas purified by flash chromatography through a silica gel column with dichloromethane and methanol (95:5 v/v)