Pyridine → (1R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-one O-methyl oxime

HRID 527100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527100
[CH3:1][C:2]1([CH3:10])[C@@H:7]2[CH2:8][C@H:3]1[CH2:4][CH2:5][C:6]2=O.Cl.[CH3:12][O:13][NH2:14].N1C=CC=CC=1>C(O)C>[CH3:12][O:13][N:14]=[C:6]1[CH2:5][CH2:4][C@H:3]2[CH2:8][C@@H:7]1[C:2]2([CH3:10])[CH3:1]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 157139Bicyclo(3.1.1)heptan-2-one, 6,6-dimethyl-, (1S,5R)-HCID 521874O-Methylhydroxylamine hydrochloride

Produkt 1

HCID 86667458(1R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-one O-methyl oximeAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of (1S,5R)-6,6-dimethylnorpinan-2-one (3.09 g, 22.35 mmol) in ethanol (70 mL) was added O-methylhydroxylamine hydrochloride (2.05 g, 24.59 mmol) and pyridine (1.29 mL, 15.92 mmol). Heated reaction mixture to 80° C. for 4 hours. Removed solvent under reduced pressure. Diluted residue with 1N HCl and extracted twice with ether. The combined organic phases were washed with aqueous saturated NaHCO3, dried (MgSO4), filtered, concentrated in vacuo to afford 3.36 g of a colorless oil (mixture of oxime isomers) that was used without further purification.

Aufarbeitung

  1. temperatureHeated
  2. customreaction mixture to 80° C. for 4 hours
  3. extractionDiluted residue with 1N HCl and extracted twice with ether
  4. washThe combined organic phases were washed with aqueous saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6f37c791837641a2b71ac2f1182de2ee
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345708B2

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