Water → 5-(Benzyloxy)-2,3-dihydro-1H-indole

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Reaction Steps

This example was carried out in analogy to: Gordon W. Gribble, Joseph H. Hoffmann Synthesis 1977, 859-860. To a precooled solution of 22.3 g (0.1 mol) 5-benzyloxyindole in 270 ml acetic acid, 19 g (0.3 mol) NaCNBH3 were added. The solution was stirred at RT for 2 h, the volume was reduced to a third and poured into 300 ml water. Potassium hydroxide was added under cooling, and the solution was extracted with ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated to yield 20.1 g (89%) 5-Benzyloxy-2,3-dihydro-1H-indole as colorless oil, MS: 225 (M).

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