반응 #52267

반응 방정식

3-(5-nitro-indol-1-yl)-hexanoic acid ethyl ester

hydrogen

→

title compound

수율 78.1%

3-(5-Amino-indol-1-yl)-hexanoic acid ethyl ester

수율 78.1%

용매

ethanol

반응 조건

후처리

1. 1
   여과The mixture was filtered through Celite
2. 2
   세척the Celite was washed with methanol
3. 3
   세척The filtrate and washing
4. 4
   농축concentrated
5. 5
   기타flash chromatographed on silica gel
6. 6
   세척eluting with EtOAc/DCM (20, 30%)

실험 절차

A mixture of 3-(5-nitro-indol-1-yl)-hexanoic acid ethyl ester (1.49 g, 4.9 mmol), and 10% palladium on activated carbon (149 mg) in ethanol (15 mL) was hydrogenated in a hydrogen balloon for 2 days. The mixture was filtered through Celite, and the Celite was washed with methanol. The filtrate and washing were combined, concentrated, and flash chromatographed on silica gel, eluting with EtOAc/DCM (20, 30%) to afford the title compound (1.05 g, 78% yield) as dark brown oil. 1H NMR (CDCl3) δ 7.22 (d, 1H, J=8.7 Hz), 7.05 (d, 1H, J=3.2 Hz), 6.90 (d, 1H, J=2.3 Hz), 6.66 (dd, 1H, J=2.2, 8.7 Hz), 6.33 (d, 1H, J=3.2 Hz), 4.78-4.73 (m, 1H), 4.02-3.96 (m, 2H), 3.47 (bs, 2H), 2.87-2.74 (m, 2H), 1.94-1.87 (m, 1H), 1.84-1.77 (m, 1H), 1.27-1.09 (m, 2H), 1.08 (t, 3H, J=7.1 Hz), 0.85 (t, 3H, J=7.3 Hz).

출처