Water → 3-(4-ethoxycarbonylbutyl)N-(3-pyridyl)-indole

Participants

Reaction Steps

To a solution of 0.5 g of 3-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)-indole in 15 ml of methylene chloride are added first 0.40 g of aluminum chloride and subsequently 0.175 g of dimethylamine borane complex. The reaction mixture is stirred at room temperature for 24 hours. The mixture is cooled to 0° and 10 ml of water are added dropwise. After ten minutes, 35 ml of 1N aqueous sodium hydroxide are added to adjust pH to 8. The methylene chloride layer is separated, the aqueous layer is further extracted with methylene chloride; the methylene chloride extracts are combined, washed with water, dried and evaporated to dryness to yield 3-(4-ethoxycarbonylbutyl)N-(3-pyridyl)-indole. Hydrolysis with dilute sodium hydroxide yields 3-(4-carboxybutyl)-N-(3-pyridyl)-indole.

Provenance & Evidence