Hydrochloric Acid → 2-(1-(3-Pyridinyl)-2-nitroethyl)-1-azabicyclo[2.2.2]octan-3-one

HRID 15378

Reaktionsgleichung

Reaktionsgleichung von HRID 15378
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[C:8]2[C:13](=[O:14])[CH:12]3[CH2:15][CH2:16][N:9]2[CH2:10][CH2:11]3)[CH:2]=1.C[O-].[Na+].[N+:20]([CH3:23])([O-:22])=[O:21].Cl>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH:8]2[C:13](=[O:14])[CH:12]3[CH2:11][CH2:10][N:9]2[CH2:16][CH2:15]3)[CH2:23][N+:20]([O-:22])=[O:21])[CH:2]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 6118222-(Pyridin-3-ylmethylidene)-1-azabicyclo[2.2.2]octan-3-oneHCID 10942334Sodium Methoxide

Produkt 1

HCID 684435732-(1-(3-Pyridinyl)-2-nitroethyl)-1-azabicyclo[2.2.2]octan-3-oneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2-((3-Pyridinyl)methylene)-1-azabicyclo[2.2.2]octan-3-one (6.4 g, 0.024 mol) in dry methanol (45 mL) was added drop-wise to sodium methoxide (produced in situ, 0.036 mol). Nitromethane (3.7 mL, 0.068 mol) was then added, and the mixture was heated at reflux for 3 h. After cooling to room temperature, 1 N HCl was slowly added to adjust pH to 8. The mixture was concentrated by rotary evaporation to yield a solid brown residue. The residue was purified by column chromatography, using ethyl acetate/hexane (1:1, v/v), followed by chloroform/methanol/ammonia (90:10:1, v/v), as eluent, to obtain a yellow oil (4.2 g, 64%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationThe mixture was concentrated by rotary evaporation
  4. customto yield a solid brown residue
  5. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-79f9c33d2aec480092cc440e638fd2c7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732607B2

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