反应 #80793

反应方程式

hydrogen

hydrogen

2-Methoxycarbonyl-3-methylquinoline

→

cis-2-methoxycarbonyl-3-methyltetrahydroquinoline

收率 78.2%

溶剂

acetic acid

反应条件

后处理

1. 1
   其他was consumed
2. 2
   浓缩concentrated in vacuo
3. 3
   其他The residue was purified by silica gel column chromatography with 20:1 to 10:1 hexane/ethyl acetate

实验过程

2-Methoxycarbonyl-3-methylquinoline (30 g, 0.149 mol) in acetic acid (300 mL) was hydrogenated over platinum oxide (1 g) under atmospheric pressure of hydrogen at room temperature until the theoretical amount of hydrogen was consumed. The mixture was passed through celite and concentrated in vacuo. The residue was purified by silica gel column chromatography with 20:1 to 10:1 hexane/ethyl acetate to give 23.93 g of cis-2-methoxycarbonyl-3-methyltetrahydroquinoline (78%): 1H NMR (270 MHz, CDCl3) d 6.99 (m, 2H), 6.64 (t, 1H, J=7.9 Hz), 6.58 (d, 1H, J=7.9 Hz), 4.34 (s, 1H), 4.09 (t, 1H, J=2.5 Hz), 3.06 (dd, 1H, J =16.9, 5.8 Hz), 2.55 (m, 1H), 2.50 (dd, 1H, J=16.9, 3.3 Hz), 0.88 (d, 3H, J=6.9 Hz).

来源