Water → 4-(2-Methyl-butyl)-benzylamine

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Reaction Steps

Under a nitrogen atmosphere, add a mixture of 4-(1-methanesulfonyloxy-2-methyl-butyl)-benzonitrile (1.3 g, 4.9 mmol) in diethyl ether (5 mL) to a slurry of lithium aluminum hydride (820 mg, 19.5 mmol) in diethyl ether (25 mL) at 0° C. Heat the mixture under reflux for 1 h. Cool the mixture in an ice-bath and add water (0.9 mL), 15% aqueous NaOH (0.9 mL) and water (2.8 mL). Apply the mixture to a silica gel column eluting with dichloromethane and 5:1 dichloromethane in chloroform/methanol/concentrated ammonium hydroxide (80:18:2) to provide the title compound (450 mg, 52%). MS (ES+) m/z: 178 (M+H)+.

Provenance & Evidence