Reaktion #79619

Reaktionsgleichung

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

lithium aluminum hydride THF

H2SO4

→

subtitled product

Ausbeute 46.0%

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

Ausbeute 46.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise at a rate which
2. 2
   Sonstigethe temperature below 26° C
3. 3
   workup.WAITAfter an additional 45 minutes
4. 4
   Sonstigethe 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
   Sonstigethe layers separated
7. 7
   ExtraktionThe organic layer was extracted with brine
8. 8
   Trocknendried over sodium sulfate
9. 9
   Sonstigeevaporated in vacuo
10. 10
    SonstigeThe residue was chromatographed on silica gel eluting with 9:1:0.1 CH2Cl2/MeOH/NH4OH

Vorschrift

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

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