Aluminium lithium hydride → 1-(2-(1-Methylpyrrolidin-2-yl)ethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-amine
Reaktionsgleichung
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]([CH2:12][CH2:13][CH:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH3:19])[C:7](=O)[CH2:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:19][N:15]1[CH2:16][CH2:17][CH2:18][CH:14]1[CH2:13][CH2:12][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:4]2[CH:3]=[C:2]([NH2:1])[CH:21]=[CH:20][C:5]1=2Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of compound 3 (825 mg, 2.87 mmol) in anhydrous THF (15 mL) was cooled to 0° C. and treated drop wise with LiAlH4 (1.0 M in THF, 11.5 mL, 11.5 mmol). The reaction mixture was warmed to room temperature and stirred overnight (23 h). The reaction mixture was cooled to 0° C. and quenched with H2O (0.4 mL), 2 N NaOH (0.4 mL), and additional H2O (0.4 mL) and stirred for 30 minutes upon, which a white precipitate formed. The solid was filtered off and washed with CH2Cl2 (2×50 mL) and the filtrate concentrated. The crude product was purified by column chromatography (2N NH3 in MeOH:CH2Cl2, 5:95) to give compound 4 (590 mg, 75%) as a thick brown syrup.