Sodium Hydroxide → 1-Aminomethyl-1-hydroxy-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Steps

5-Methoxy-3-phenyl-1,2,3,4-tetrahydro-1-naphthalenone (1.9 g, 7.5 mmol), the product of Example 1, 3 mL of acetonitrile, 1.9 g (19 mmol) of trimethylsilylcyanide, commercially available from Aldrich Chemical Company, and 100 mg of aluminum chloride were mixed together and heated at reflux temperature for 2 h. The reaction mixture was cooled and concentrated. The residue was dissolved in 6 mL of diethyl ether and the ether solution was added dropwise to a solution of 0.62 g (16 mmol) of lithium aluminum hydride in 14 mL of diethyl ether. After the reaction mixture was heated at reflux temperature for 2 h, 0.6 mL of water was added dropwise, followed by 0.6 mL of 15% aqueous sodium hydroxide solution, followed by 1.8 mL of water. The reaction mixture was stirred until a granular precipitate formed. The solid was filtered and washed with 3×20 mL of methylene chloride. The filtrate was concentrated to give 2.0 g (95% yield) of the title compound as an oil; 1H NMR (d6-DMSO) δ 1.90 (t, 1H), 2.25 (dt, 1H), 2.65-2.85 (m, 2H), 2.95-3.25 (m, 3H), 3.78 (s, 3H), 6.85-7.05 (m, 3H), 7.2-7.5 (m, 5H).

Provenance & Evidence