Reaktion #65651

Reaktionsgleichung

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

ozone

→

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

Ausbeute 80.0%

Lösungsmittel

methylene chloride

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedegas with nitrogen for 20 minutes
2. 2
   workup.ADDITIONadd pyridine (0.2 mL)
3. 3
   SonstigeQuench with dimethylsulfide (4 mL)
4. 4
   workup.ADDITIONDilute with methylene chloride (75 mL)
5. 5
   Waschenwash with 5% sulfuric acid (40 mL) and brine (40 mL)
6. 6
   TrocknenDry (Na2SO4)
7. 7
   Sonstigeevaporate the solvent in vacuo
8. 8
   Sonstigepurify by chromatography (hexane/ethyl acetate)

Vorschrift

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%).

Quelle