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

HRID 23989노트

반응식

HRID 23989 반응식
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH:6]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([N+:19]([O-])=O)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)[CH2:7][CH2:8][CH3:9])[CH3:2].[H][H]>[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH:6]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)[CH2:7][CH2:8][CH3:9])[CH3:2]

참가 물질

5

반응물 2

HCID 674273143-(5-Nitro-indol-1-yl)-hexanoic acid ethyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 674273453-(5-Amino-indol-1-yl)-hexanoic acid ethyl ester수율 78.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

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).

후처리

  1. filtrationThe mixture was filtered through Celite
  2. washthe Celite was washed with methanol
  3. washThe filtrate and washing
  4. concentrationconcentrated
  5. customflash chromatographed on silica gel
  6. washeluting with EtOAc/DCM (20, 30%)

출처 및 근거

ORD 기록
ord-ca9a8eb9d14b4fccb820cea6e97fe820
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855722B2

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