5-octyl-1H-indole → 5-Octylindoline

Beteiligte Stoffe

Reaktionsschritte

To a solution of the product of Step B (0.08 g; 0.35 mmol) in AcOH (1.5 ml) NaBH3CN was added at 0° C., with stirring. The resulting mixture was stirred for 2 h at room temperature, then diluted to 20 ml with diethyl ether and washed with 10% NaOH (2×5 ml), H2), brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by FCC (SiO2; hexane/EtOAc; 9:1) to give the title compound (0.05 g; 62%) as a colourless syrup. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=7 Hz); 1.26 (m, 10H); 1.54 (m, 2H); 2.48 (tr, 2H, J=7.9 Hz); 2.98 (tr, 2H, 9.2 Hz) 3.52 (tr, 2H, J=9.2 Hz); 6.56 (d, 1H, 7.8 Hz); 6.83 (d, 1H, J=7.8 Hz); 6.93 (s, 1H).

Herkunft & Nachweise