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

HRID 1295126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295126
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 674273453-(5-Amino-indol-1-yl)-hexanoic acid ethyl esterAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-58c6a94439d24fdebbe05292404df134
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241789B2

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