1-ethoxycarbonyl-4-(1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane → 1-ethoxycarbonyl-4-(1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

HRID 1584436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1584436
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:17]([CH2:18][C:19]3[O:20][C:21]([C:24](OCC)=[O:25])=[CH:22][CH:23]=3)[C:16]3[CH:29]=[CH:30][CH:31]=[CH:32][C:15]=3[N:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:17]([CH2:18][C:19]3[O:20][C:21]([CH2:24][OH:25])=[CH:22][CH:23]=3)[C:16]3[CH:29]=[CH:30][CH:31]=[CH:32][C:15]=3[N:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 184644291-ethoxycarbonyl-4-(1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepaneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 184645131-ethoxycarbonyl-4-(1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Combine 1-ethoxycarbonyl-4-(1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane (5 mmol) and lithium aluminum hydride (5 mmol) in tetrahydrofuran. Heat to reflux. After 12 hour, cool and carefully quench the reaction mixture with 10% aqueous ammonium chloride solution. Extract the reaction mixture with ethyl acetate. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give 1-ethoxycarbonyl-4-(1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane.

Aufarbeitung

  1. temperatureHeat to reflux
  2. temperaturecool
  3. customcarefully quench the reaction mixture with 10% aqueous ammonium chloride solution
  4. extractionExtract the reaction mixture with ethyl acetate
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4f636fb3d33144eb869b0665022cf610
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05932571

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