반응 #65651

반응 방정식

2-(1,3-dihydro-l,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-hexenylamine

ozone

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2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-oxo-pentylamine

수율 80.0%

용매

methylene chloride

methanol

반응 조건

후처리

1. 1
   기타degas with nitrogen for 20 minutes
2. 2
   workup.ADDITIONadd pyridine (0.2 mL)
3. 3
   기타Quench with dimethylsulfide (4 mL)
4. 4
   workup.ADDITIONDilute with methylene chloride (75 mL)
5. 5
   세척wash with 5% sulfuric acid (40 mL) and brine (40 mL)
6. 6
   건조Dry (Na2SO4)
7. 7
   기타evaporate the solvent in vacuo
8. 8
   기타purify by chromatography (hexane/ethyl acetate)

실험 절차

Dissolve 2-(1,3-dihydro-l,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-hexenylamine (1.2 g, 3.19 mmol) in methylene chloride (40 mL) and methanol (4 mL) and cool to -78° C. under a nitrogen atmosphere. Treat with ozone until a blue color persists, degas with nitrogen for 20 minutes and add pyridine (0.2 mL). Quench with dimethylsulfide (4 mL) and stir overnight at room temperature. Dilute with methylene chloride (75 mL) and wash with 5% sulfuric acid (40 mL) and brine (40 mL). Dry (Na2SO4) , evaporate the solvent in vacuo and purify by chromatography (hexane/ethyl acetate) to give 2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-oxo-pentylamine as a white solid (972 mg, 80%).

출처