반응 #2335294

반응 방정식

1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine

cyanogen bromide

sodium bicarbonate

→

3-cyano-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine

수율 70.0%

용매

chloroform

chloroform

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux for 2.6 hr, under nitrogen
3. 3
   기타the layers were separated
4. 4
   세척The organic layer was washed with sodium bicarbonate solution
5. 5
   추출The combined aqueous layers were back extracted with ether
6. 6
   세척the combined organic layers were washed with brine
7. 7
   건조dried over anhydrous potassium carbonate
8. 8
   여과filtered
9. 9
   농축The filtrate was concentrated
10. 10
    기타The residue was purified by flash chromatography (silica gel, 2% triethylamine/ether)

실험 절차

To a stirred solution of 0.50 g of cyanogen bromide and 20 ml of chloroform was added, at room temperature with stirring, a solution of 1.0 g of 1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine and 40 ml of chloroform. The mixture was heated at reflux for 2.6 hr, under nitrogen, and then cooled to room temperature. Dilute aqueous sodium bicarbonate solution was added and the layers were separated. The organic layer was washed with sodium bicarbonate solution. The combined aqueous layers were back extracted with ether, and the combined organic layers were washed with brine, dried over anhydrous potassium carbonate and filtered. The filtrate was concentrated. The residue was purified by flash chromatography (silica gel, 2% triethylamine/ether) to afford 0.73 g (70%) of 3-cyano-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine, which was combined with 0.39 g of the product from a previous reaction.

출처