반응 #1972918

반응 방정식

10-chloro-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

→

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

수율 162.5%

용매

chloroform

chloroform

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux for 2 hr, under nitrogen
3. 3
   기타the layers separated
4. 4
   추출The organic layer was extracted with dilute aqueous 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
   농축The filtrate was concentrated
10. 10
    기타the residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate)

실험 절차

To a stirred solution of 1.68 g of cyanogen bromide and 35 ml of chloroform was added, at room temperature with stirring under nitrogen, a solution of 3.8 g of 10-chloro-1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine and 100 ml of chloroform. The mixture was heated at reflux for 2 hr, under nitrogen, and cooled to room temperature. Dilute aqueous sodium bicarbonate solution was added and the layers separated. The organic layer was extracted with dilute aqueous sodium bicarbonate solution. The combined aqueous layers were extracted with ether and the combined organic layers were washed with brine, dried over anhydrous potassium carbonate and filtered. The filtrate was concentrated and the residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate) to afford 6.41 g (78%) of 10-chloro-3-cyano-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo-[3,2-h][3]benzazocine.

출처