반응 #1972914

반응 방정식

nitrile

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

lithium aluminium hydride

→

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

수율 69.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도to warm to room temperature
2. 2
   온도was then heated
3. 3
   온도at reflux for 2 hr
4. 4
   온도The mixture was cooled to room temperature
5. 5
   여과The mixture was filtered through anhydrous sodium sulfate
6. 6
   세척The filter cakes were washed with a mixture of triethylamine/methanol/ethyl acetate
7. 7
   농축the filtrate was concentrated
8. 8
   기타The residue was purified by flash chromatography (alumina, triethyl amine/methanol/ether)

실험 절차

The nitrile (1.12 g) was dissolved in 60 ml of tetrahydrofuran and 0.80 g of lithium aluminium hydride was added, with cooling to 0° C. under nitrogen. The mixture was allowed to warm to room temperature and was then heated at reflux for 2 hr. The mixture was cooled to room temperature and 10% aqueous tetrahydrofuran was added. The mixture was filtered through anhydrous sodium sulfate and then celite. The filter cakes were washed with a mixture of triethylamine/methanol/ethyl acetate, and the filtrate was concentrated. The residue was purified by flash chromatography (alumina, triethyl amine/methanol/ether) to afford 0.70 g (69%) of 6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine.

출처