반응 #79619

반응 방정식

9-benzyl-4-cyanomethyloxy-2-methoxycarbazole-5-carboxamide

lithium aluminum hydride THF

H2SO4

→

subtitled product

수율 46.0%

4-(2-amino)ethyloxy-9-benzyl-2-methoxycarbazole-5-carboxamide

수율 46.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise at a rate which
2. 2
   기타the temperature below 26° C
3. 3
   workup.WAITAfter an additional 45 minutes
4. 4
   기타the reaction was quenched with 0.32 ml 1:1 THF/H2O, 0.48 ml 13% NaOH, and finally 51 μl H2O
5. 5
   workup.ADDITIONThe reaction was diluted with EtOAc and saturated NaHCO3
6. 6
   기타the layers separated
7. 7
   추출The organic layer was extracted with brine
8. 8
   건조dried over sodium sulfate
9. 9
   기타evaporated in vacuo
10. 10
    기타The residue was chromatographed on silica gel eluting with 9:1:0.1 CH2Cl2/MeOH/NH4OH

실험 절차

To 1.25 ml (1.25 mmol) 1M lithium aluminum hydride/THF in 8.3 ml THF at 0° C. was added H2SO4(34.5 μl, 0.63 mmol) dropwise over 5 min. The mixture was allowed to stir at room temperature 1 hour, then a suspension of 9-benzyl-4-cyanomethyloxy-2-methoxycarbazole-5-carboxamide (0.32 g, 0.83 mmol) in 8.3 ml THF was added dropwise at a rate which kept the temperature below 26° C. After an additional 45 minutes, the reaction was quenched with 0.32 ml 1:1 THF/H2O, 0.48 ml 13% NaOH, and finally 51 μl H2O. The reaction was diluted with EtOAc and saturated NaHCO3, and the layers separated. The organic layer was extracted with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 9:1:0.1 CH2Cl2/MeOH/NH4OH to give the subtitled product (148 mg, 46%). MS (ES+) 390

출처