Sulfuric Acid → 5-(2-Amino)ethyloxy-9-benzyl-7-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide

HRID 51340

Reaktionsgleichung

Reaktionsgleichung von HRID 51340
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.OS(O)(=O)=O.[CH2:17]([N:24]1[C:36]2[CH2:35][CH2:34][CH2:33][CH:32]([C:37]([NH2:39])=[O:38])[C:31]=2[C:30]2[C:25]1=[CH:26][C:27]([O:44][CH3:45])=[CH:28][C:29]=2[O:40][CH2:41][C:42]#[N:43])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[NH2:43][CH2:42][CH2:41][O:40][C:29]1[CH:28]=[C:27]([O:44][CH3:45])[CH:26]=[C:25]2[C:30]=1[C:31]1[CH:32]([C:37]([NH2:39])=[O:38])[CH2:33][CH2:34][CH2:35][C:36]=1[N:24]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 101349259-Benzyl-7-methoxy-5-cyanomethyloxy-1,2,3,4-tetrahydrocarbazole-4-carboxamideHCID 68718528lithium aluminium hydride THF

Produkt 1

HCID 227391325-(2-Amino)ethyloxy-9-benzyl-7-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamideAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 1.93 ml (1.93 mmol) 1M lithium aluminum hydride/THF in 13 ml THF at 0° C. was added H2SO4(53 μl, 0.97 mmol) dropwise over 5 min. The mixture was allowed to stir at room temperature 1 hour, then a solution of 9-benzyl-7-methoxy-5-cyanomethyloxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide (0.50 g, 1.29 mmol) in 13 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 0.5 ml 1:1 THF/H2O, 0.75 ml 13% NaOH, and finally 80 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 (0.28 g, 55%). MS (ES+) 394

Aufarbeitung

  1. customthe temperature below 26° C
  2. waitAfter an additional 45 minutes
  3. customthe reaction was quenched with 0.5 ml 1:1 THF/H2O, 0.75 ml 13% NaOH, and finally 80 μl H2O
  4. additionThe reaction was diluted with EtOAc and saturated NaHCO3
  5. customthe layers separated
  6. extractionThe organic layer was extracted with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on silica gel eluting with 9:1:0.1 CH2Cl2/MeOH/NH4OH

Quellen und Nachweise

ORD-Eintrag
ord-b3c0a4b14992469eaa6f497fccc83053
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713645B1

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