Aluminium lithium hydride → 3-Cyclopentyloxy-4-methoxyphenethylamine

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (10.83 g, 28.5 mmol) in ether (250 mL) at 0° C. under an argon atmosphere was added dropwise a solution of 3-cyclopentyloxy-4-methoxy-β-nitrostyrene (15.00 g, 57.0 mmol) in tetrahydrofuran (85 mL). The resulting mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was cooled to 0° C. and quenched by the successive dropwise addition of water (11 mL), 15% sodium hydroxide (11 mL) and water (33 mL). The mixture was filtered through a pad of Celite™ and the filtrate was washed successively with water, 10% hydrochloric acid and water. The aqueous washes were combined, made basic with saturated aqueous potassium carbonate and extracted three times with ether and twice with methylene chloride. The organic layers were combined and dried (potassium carbonate). Removal of the solvent in vacuo provided the amine (10.80 g, 81%). A portion of the crude amine was purified by flash chromatography, eluting with 1:10:90 water/methanol/chloroform.

Provenance & Evidence