反応 #65651

反応方程式

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

収率 80.0%

溶媒

methylene chloride

methanol

反応条件

後処理

1. 1
   その他degas with nitrogen for 20 minutes
2. 2
   workup.ADDITIONadd pyridine (0.2 mL)
3. 3
   その他Quench with dimethylsulfide (4 mL)
4. 4
   workup.ADDITIONDilute with methylene chloride (75 mL)
5. 5
   洗浄wash with 5% sulfuric acid (40 mL) and brine (40 mL)
6. 6
   乾燥Dry (Na2SO4)
7. 7
   その他evaporate the solvent in vacuo
8. 8
   その他purify by chromatography (hexane/ethyl acetate)

実験手順

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%).

出典