반응 #1738799

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

diisopropylethylamine

chloroform

chloroform

→

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

수율 95.0%

용매

sodium bicarbonate

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux for 2.6 hr
3. 3
   기타the layers were separated
4. 4
   세척The organic layer was washed with sodium bicarbonate solution
5. 5
   추출The combined aqueous layers were 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
   기타Concentration of the filtrate followed by purification by flash chromatography (silica gel, 2% triethylamine/ethyl acetate)

실험 절차

To a stirred solution of 6.81 g of cyanogen bromide, 4.7 ml of diisopropylethylamine, and 142 ml of chloroform was added, at room temperature with stirring, a solution of 13.7 g of 1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine and 414 ml of chloroform. The mixture was heated at reflux for 2.6 hr, cooled to room temperature, diluted with aqueous sodium bicarbonate solution, and the layers were separated. The organic layer was washed with sodium bicarbonate solution. The combined aqueous layers were extracted with ether. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, and filtered. Concentration of the filtrate followed by purification by flash chromatography (silica gel, 2% triethylamine/ethyl acetate) afforded 13.5 g (95%) of 3-cyano-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine.

출처