反应详情

温度

0 °C

To 5.4 ml (5.39 mmol) of a 1M phenyl-magnesium bromide solution under nitrogen at 0° C., was added drop-wise a solution of 500 mg 8-methyl-8-aza-bicyclo[3.2.1]octan-2-one (CAS 78477-91-5) in 5 ml tetrahydrofuran over mol-sieve. The reaction mixture was stirred at 0° C. for 5 hours. The mixture was quenched under ice bath cooling with a 20% ammonium chloride solution (5 ml). The organic layer was separated and the aqueous layer was extracted once with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica (20 g) eluting with a gradient formed from n-heptane and ethyl acetate (0 to 100%) to provide 508 mg (65.1%) of the title compound as a light yellow oil. MS (m/e): 218.4 (M+H+).

1. customThe mixture was quenched under ice bath
2. temperaturecooling with a 20% ammonium chloride solution (5 ml)
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted once with ethyl acetate
5. washThe combined organic layers were washed with water
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude oil was purified with flash column chromatography on silica (20 g)
10. washeluting with a gradient
11. customformed from n-heptane and ethyl acetate (0 to 100%)