[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1([CH3:27])[CH2:16][C:15]2[NH:14][CH:13]=[C:12]([CH2:17][CH2:18][C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=O)[C:11]=2[C:10](=O)[CH2:9]1>C1COCC1.[OH-].[Na+].O>[CH3:27][C:8]1([CH3:7])[CH2:16][C:15]2[NH:14][CH:13]=[C:12]([CH2:17][CH2:18][CH2:19][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:11]=2[CH2:10][CH2:9]1
LAH (0.57 g, 15.1 mmol) was added dropwise to a suspension of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethylpropionamide (1.1 g, 3.8 mmol) in THF (80 mL). The mixture was refluxed overnight. The reaction was cooled and ice was added until no more gas was generated. A few drops of 15% NaOH in water was then added. The mixture was stirred at room temperature for 30 minutes and then filtered to remove insolubles. The filtrate was concentrated to give 0.9 g of [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethyl-amine as a light yellow oil.
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