5-benzyloxy-3-(2-nitro-propyl)-1H-indole → 1-methyl-2-(5-benzyloxy-1H-indol-3-yl)ethyl amine

Participants

Reaction Steps

To a stirred suspension of lithium aluminum hydride (700 mg) in diethyl ether (25 mL) was slowly added a solution of 5-benzyloxy-3-(2-nitro-propyl)-1H-indole (650 mg) in diethyl ether (10 mL). The mixture was refluxed for 2 h. After cooling to rt, the reaction was quenched sequentially with 0.7 mL water, 0.7 mL 3 M aqueous sodium hydroxide, followed by 1.4 mL of water. The mixture was stirred at rt for 30 min and filtered. The filtrate was evaporated to afford 2-(5-benzyloxy-1H-indol-3-yl)-1-methyl-ethylamine (300 mg).

Provenance & Evidence