反応 #68980

反応方程式

3-Trifluoromethanesulfonyloxy-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester

dichloromethane

dioxane

water

water

diisopropyl-ethylamine

→

8-Azabicyclo[3.2.1]oct-2-ene-3,8-dicarboxylic acid 8-tert-butyl ester

反応条件

後処理

1. 1
   抽出The organic phase is extracted with a saturated aqueous NaHCO3 solution
2. 2
   抽出extracted with ethyl acetate
3. 3
   洗浄The organic phase is washed with water
4. 4
   乾燥with a saturated aqueous sodium chloride solution and dried over MgSO4
5. 5
   濃縮After concentrating to dryness, 2.7 g of expected 8-aza-bicyclo[3.2.1]oct-2-ene-3,8-dicarboxylic acid 8-tert-butyl ester
6. 6
   その他are obtained

実験手順

3-Trifluoromethanesulfonyloxy-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester (2.0 g, 5.6 mmol), hexacarbonylmolybdenum (0.74 g, 2.8 mmol), palladium diacetate (0.13 g, 0.56 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.31 g, 0.56 mmol), 4-dimethylaminopyridine (1.37 g, 11.2 mmol) and diisopropyl-ethylamine (2.24 ml, 12.9 mmol) are placed in 2.0 ml of water and 12 ml of dioxane in a microwave reaction vessel. The medium is microwave-heated at 150° C. for 10 min. The crude product is taken up with water and with dichloromethane. The organic phase is extracted with a saturated aqueous NaHCO3 solution. The aqueous phase is acidified with KHSO4 and then extracted with ethyl acetate. The organic phase is washed with water and then with a saturated aqueous sodium chloride solution and dried over MgSO4. After concentrating to dryness, 2.7 g of expected 8-aza-bicyclo[3.2.1]oct-2-ene-3,8-dicarboxylic acid 8-tert-butyl ester are obtained.

出典