反応 #80793

反応方程式

hydrogen

hydrogen

2-Methoxycarbonyl-3-methylquinoline

→

cis-2-methoxycarbonyl-3-methyltetrahydroquinoline

収率 78.2%

溶媒

acetic acid

反応条件

後処理

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

実験手順

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).

出典