Sodium cyanoborohydride → 5-(3,4,5-Trimethoxyphenethyl)indoline
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2.[BH3-]C#N.[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH2:12][CH2:11]2Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of the product of Step B (0.12 g; 0.38 mmol) in tetrahydrofuran (THF)/acetic acid 1:1 mixture (6 ml) NaBH3CN (0.1 g; 1.16 mmol) was added at room temperature. After stirring for 1 h the solvents were removed in vacuo and the residue was diluted to 15 ml with Et2O and washed with 1 N NaOH (5 ml), H2O (2×5 ml), brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure to give the title compound (0.12 g; 100%), which was used in next step without further purification. 1H-NMR (CDCl3) 2.85 (s, 4H); 2.99 (tr, 2H, J=8.3 Hz); 3.52 (tr, 2H, J=8.3 Hz); 3.66 (broad s, 1H); 3.8 (s, 9H); 6.39 (s, 2H); 6.57 (d, 1H, J=7.9 Hz); 6.84 (d, 1H, J=7.9 Hz); 6.96 (s, 1H).