Borane;tetrahydrofuran → (3,4-Dimethyl-phenyl)-[2-(5-methyl-pyridin-2-yl)-ethyl]-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 390 mg (1.5 mmol) N-(3,4-dimethyl-phenyl)-2-(5-methyl-pyridin-2-yl)-acetamide in 8 mL THF under argon at ambient temperature, was added dropwise 3.1 mL (3.1 mmol) of a 1 M borane-tetrahydrofuran solution. The solution was refluxed for 5 hours, cooled to 0° C. and quenched with 7 mL of a 20% NH4Cl solution. The solution was acidified with HCl 5N and stirred at ambient temperature for 1.5 hours. The residue was basified with a sat. NaHCO3 solution, and concentrated. The residue was dissolved in ethylacetate, the aqueous phase was extracted 2 times with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.038 g (10%) of the title compound as a yellow oil. MS (m/e): 241.3 [M+H]+.

Provenance & Evidence