反应详情

温度

0 °C

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]+.

1. temperatureThe solution was refluxed for 5 hours
2. customquenched with 7 mL of a 20% NH4Cl solution
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in ethylacetate
5. extractionthe aqueous phase was extracted 2 times with ethyl acetate
6. dry with materialThe combined extracts were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
10. customformed from heptane and ethylacetate