Sodium borohydride → 1-benzyl-4-methyl-2,3,9,9a-tetrahydro-1H-indeno[2,1-b]pyridine

HRID 455361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455361
[BH4-].[Na+].[Br-].[CH2:4]([N+:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[CH2:24][C:12]=12)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C>[CH2:4]([N:11]1[CH2:16][CH2:15][C:14]([CH3:17])=[C:13]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[CH2:24][CH:12]12)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 671942071-benzyl-4-methyl-9H-indeno[2,1-b]pyridinium bromide

Produkt 1

HCID 582946471-benzyl-4-methyl-2,3,9,9a-tetrahydro-1H-indeno[2,1-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Sodium borohydride (0.15 g) is added to a suspension of 1-benzyl-4-methyl-9H-indeno[2,1-b]pyridinium bromide (0.92 g) in ethanol (10 mL) chilled in an ice bath. The cooling bath is removed and the mixture is stirred at room temperature for 1 h and at 60° C. for 2 h. More sodium borohydride (0.18 g) is added and stirring is continued at reflux temperature for 4 h. After the addition of another portion of sodium borohydride (0.10 g), the mixture is stirred at reflux temperature overnight. After cooling to room temperature, ice-cold water is added and the precipitate is separated by filtration. The precipitate is dissolved in ether, the resulting solution is dried (Na2SO4), and the solvent is evaporated to afford the crude product that is used without further purification. Yield: 0.66 g (crude); Mass spectrum (ESI+): m/z=276 [M+H]+.

Aufarbeitung

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. additionMore sodium borohydride (0.18 g) is added
  4. stirringstirring
  5. temperatureat reflux temperature for 4 h
  6. additionAfter the addition of another portion of sodium borohydride (0.10 g)
  7. stirringthe mixture is stirred
  8. temperatureat reflux temperature overnight
  9. temperatureAfter cooling to room temperature
  10. additionice-cold water is added
  11. customthe precipitate is separated by filtration
  12. dissolutionThe precipitate is dissolved in ether
  13. dry with materialthe resulting solution is dried (Na2SO4)
  14. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ecba9cee8a09488aa4106b2b29bb4670
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497281B2

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