Methyl 3-(5-benzyloxyindolyl)propanoate → methyl 3-(5-hydroxy-1H-indol-2-yl)propanoate
Reaktionsgleichung
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:12]2)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:12]2Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of methyl 3-(5-benzyloxyindolyl)propanoate (1.1 g, 3.56 mmol), as prepared in the preceding step, 10% palladium(0) on carbon (100 mg) in ethanol was stirred under hydrogen for 3 h. The catalyst was removed by filtration, the filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (1–5% ethyl acetate in methylene chloride) to give the title compound as a pale yellow oil (700 mg, 90%). 1H-NMR (400 M Hz, CDCl3) δ 7.18 (d, J=8.8 Hz, 1H), 7.08 (d, J=3.1 Hz, 1H), 7.02 (d, J=3.2 Hz, 1H), 6.77 (dd, J=8.8, 2.5 Hz, 1H), 6.34 (d, J=3.1 Hz, 1H), 4.75 (s, 1H), 4.40 (t, J=6.9 Hz, 2H), 3.66 (s, 3H), 2.81 (t, J=6.9 Hz, 2H).