Sulfuric acid magnesium salt (1:1) → [(2S)-2-(4-Fluorophenyl)pent-4-en-1-yl]methylamine

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Reaction Steps

Combine (S)-2-(4-fluorophenyl)pent-4-enoic acid, N-methyl amide (3.1 g, 14.96 mmol) and tetrahydrofuran (35 mL). Cool in an ice bath, add a solution of lithium aluminum hydride (35 mL, 1.0 M in tetrahydrofuran, 35 mmol). After the addition is complete, heat the reaction mixture to reflux. After 2.5 hours, cool in an ice bath and carefully quench with water (1.3 mL), an aqueous 15% sodium hydroxide solution (1.3 mL), and then water (4 mL). Dilute the quenched reaction mixture with diethyl ether (75 mL) , add MgSO4, and stir. After 1 hour, filter through celite and rinse the solids with dichloromethane. Evaporate the filtrate in vacuo to give (S)-N-methyl-(2-(4-fluorophenyl)pent-4-enyl)amine: Rf=0.47 (silica gel, 18.5/1.5/0.2 dichloromethane/methanol/concentrated aqueous ammonia).

Provenance & Evidence