反应详情

2-(4-Methoxy-2,3-dimethylphenyl)-1-(pyrrolidin-1-yl)ethanone was suspended in a mixture of 48% HBr (aq) (15 mL) and acetic acid (15 mL) and the reaction was heated to reflux for 24 h. The reaction was poured over ice and brought to pH 4 with 1 N NaOH. Ethyl acetate was added and the layers were separated. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was taken up in dioxane (100 mL) and 1 N HCl (15 mL) was added. The reaction was heated to reflux for 4 days. Ethyl acetate and 1N HCl were added. The layers were separated, and the aqueous layer was washed with additional ethyl acetate. The organics were combined, dried (Na2SO4), filtered and concentrated in vacuo. Flash column chromatography of the residue, eluting 0% to 7% methanol in dichloromethane, afforded the title compound. LC-MS ESI (neg.) m/z: 179.2 (M−H).

1. temperaturethe reaction was heated
2. temperatureto reflux for 24 h
3. additionThe reaction was poured over ice
4. customthe layers were separated
5. dry with materialThe organic layer was dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. addition1 N HCl (15 mL) was added
9. temperatureThe reaction was heated
10. temperatureto reflux for 4 days
11. additionEthyl acetate and 1N HCl were added
12. customThe layers were separated
13. washthe aqueous layer was washed with additional ethyl acetate
14. dry with materialdried (Na2SO4)
15. filtrationfiltered
16. concentrationconcentrated in vacuo
17. washFlash column chromatography of the residue, eluting 0% to 7% methanol in dichloromethane