반응 #157834

반응 방정식

hydrobromic acid

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

Water

→

title compound

수율 49.2%

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

수율 49.2%

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.ADDITIONAnisole (2 mL) was added to a solution of the residue (278 mg) in trifluoroacetic acid (1 mL)
6. 6
   workup.STIRRINGthe mixture was stirred at 80° C. for 4.5 hours
7. 7
   기타The solvent was evaporated under reduced pressure
8. 8
   기타The residue was purified by silica gel column chromatography (chloroform:methanol=1:0→9:1)

실험 절차

48% hydrobromic acid (3.0 mL) was added to a solution of (5R)-5-[(E)-2-(5-acetyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (300 mg) in 1,4-dioxane (3.0 mL), and the mixture was stirred at 65° C. for 0.5 hour. Water was added to the reaction solution, 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. Anisole (2 mL) was added to a solution of the residue (278 mg) in trifluoroacetic acid (1 mL), and the mixture was stirred at 80° C. for 4.5 hours. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=1:0→9:1) to give the title compound as a yellow powder (103 mg).

출처