Sulfuric acid magnesium salt (1:1) → (S)-N-methyl-(2-phenylpent-4-enyl)amine

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Reaction Steps

Combine (S)-2-phenylpent-4-enoic acid, N-methyl amide (1.35 g, 7.13 mmol) and tetrahydrofuran (20 mL). Cool in an ice bath, add a solution of lithium aluminum hydride (17 mL, 1.0 M in tetrahydrofuran, 17 mmol). After the addition is complete, heat the reaction mixture to reflux. After 24 hours, cool in an ice bath and carefully quench with water (0.6 mL), an aqueous 15% sodium hydroxide solution (0.6 mL) and then water (2 mL). Dilute the quenched reaction mixture with diethyl ether (50 mL), add MgSO4, and stir. After 2 hours, filter through celite and rinse the solids with dichloromethane. Dry the filtrate with MgSO4, and evaporate in vacuo to give (S)-N-methyl-(2-phenylpent-4-enyl)amine: Rf=0.51 (silica gel, 18/2/0.2 dichloromethane/methanol/concentrated aqueous ammonia).

Provenance & Evidence