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

HRID 1295126ノート

反応式

HRID 1295126 の反応式
[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]

参加物

5

反応物 2

HCID 674273143-(5-Nitro-indol-1-yl)-hexanoic acid ethyl esterHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-58c6a94439d24fdebbe05292404df134
出典データセット
uspto-grants-2007_07
特許番号
US07241789B2

反応ノート

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