Water → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzofuran-2-carboxamide

HRID 15458

Reaktionsgleichung

Reaktionsgleichung von HRID 15458
[Sn](Cl)Cl.[N:4]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[C@@H:6]([NH:12][C:13]([C:15]1[O:16][C:17]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:18]=3[CH:19]=1)=[O:14])[CH2:5]2.O.[OH-].[Na+]>CN(C=O)C>[N:4]12[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11]1)[C@@H:6]([NH:12][C:13]([C:15]1[O:16][C:17]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:18]=3[CH:19]=1)=[O:14])[CH2:5]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 59341432N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzofuran-2-carboxamide

Produkt 1

HCID 10236388N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzofuran-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2.0 ml (4 mmol) of a 2 M tin(II) chloride solution in DMF are added to N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzofuran-2-carboxamide (100 mg, 0.32 mmol). The mixture is stirred overnight. The reaction mixture is poured into water and made basic using 1N aqueous sodium hydroxide solution. The aqueous phase is extracted six times with ethyl acetate. The combined organic phases are dried over magnesium sulfate, and the solvent is removed under reduced pressure using a rotary evaporator. The crude product is taken up in methanol and shaken together with acidic ion exchange resin (Dowex WX2-200) for about 20 min. The loaded ion exchanger is washed three times with in each ase 30 ml of methanol, then with water/methanol 8:2, again with methanol, with dichloromethane and finally again with methanol. The product is eluted using methanol/triethylamine 95:5. The solvent is removed under reduced pressure using a rotary evaporator. 52 mg (58% of theory) of the title compound are isolated.

Aufarbeitung

  1. extractionThe aqueous phase is extracted six times with ethyl acetate
  2. dry with materialThe combined organic phases are dried over magnesium sulfate
  3. customthe solvent is removed under reduced pressure
  4. customa rotary evaporator
  5. stirringshaken together with acidic ion exchange resin (Dowex WX2-200) for about 20 min
  6. washThe loaded ion exchanger is washed three times with in each ase 30 ml of methanol
  7. washThe product is eluted
  8. customThe solvent is removed under reduced pressure
  9. customa rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-b5bb408eeb3f4944b9d4e1a21c9dc6fa
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732477B2

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