Sodium borohydride → 4-[(3S)-3,7-dimethyl-6-octenyloxy]benzylamine

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Reaction Steps

Sodium borohydride (NaBH4, 29.4 mmol) was added to a mixture of 4-[(3S)-3,7-dimethyl-6-octenyloxy]cyanobenzene (2.52 g, 9.80 mmol) and anhydrous nickel chloride (NiCl2, 9.8 mmol) in dry ethanol (20 mL). After 2 hours the reaction mixture was filtered over Celite® and the Celite® bed was rinsed with ethanol (2×10 mL). The solution was diluted with water (150 mL) and extracted with ether (3×25 mL). The combined ethereal phase was washed with water, dried over MgSO4, and the solvent was evaporated to afford an oil which was purified by column chromatography (EtOAc-hexane) to give 4-[(3S)-3,7-dimethyl-6-octenyloxy]benzylamine as a colorless oil (1.82 g, 6.97 mmol, 71.1% yield).

Provenance & Evidence