반응 #157848

반응 방정식

hydrobromic acid

(5R)-5-[(E)-2-(4-tert-butylphenyl)-2-{5-[4-(dimethylamino)butyl]-6-methoxypyridin-2-yl}ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

sodium bicarbonate

→

title compound

6-{(E)-1-(4-tert-Butylphenyl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-[4-(dimethylamino)butyl]pyridin-2(1H)-one

용매

1,4-dioxane

반응 조건

후처리

1. 1
   추출followed by extraction with ethyl acetate
2. 2
   세척The organic layer was washed with brine
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   기타after which the solvent was evaporated under reduced pressure
5. 5
   workup.STIRRINGA solution of the residue in trifluoroacetic acid (4 mL) and anisole (2 mL) was stirred at 80° C. for five hours
6. 6
   workup.ADDITIONThe reaction solution was poured into saturated aqueous sodium bicarbonate
7. 7
   추출followed by extraction with chloroform
8. 8
   세척The organic layer was washed with brine
9. 9
   건조dried over anhydrous magnesium sulfate
10. 10
    여과filtered
11. 11
    기타after which the solvent was evaporated under reduced pressure
12. 12
    기타The residue was purified by silica gel column chromatography (chloroform:methanol=100:1→3:1)

실험 절차

48% hydrobromic acid (1.5 mL) was added to a solution of (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-{5-[4-(dimethylamino)butyl]-6-methoxypyridin-2-yl}ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one in 1,4-dioxane (2 mL), and the mixture was stirred at 65° C. for 30 minutes. The reaction solution was poured into saturated aqueous sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. A solution of the residue in trifluoroacetic acid (4 mL) and anisole (2 mL) was stirred at 80° C. for five hours. The reaction solution was poured into saturated aqueous sodium bicarbonate, followed by extraction with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:1→3:1) and solidified with diethyl ether-hexane to give the title compound as a light yellow amorphous (13 mg, 12% (four steps)).

출처