Hydroxyamine hydrochloride → 2-Methyl-1-azabicyclo[2.2.2]octan-3-one oxime

HRID 1017648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017648
Cl.[CH3:2][CH:3]1[C:8](=O)[CH:7]2[CH2:10][CH2:11][N:4]1[CH2:5][CH2:6]2.Cl.[NH2:13][OH:14].O.O.O.C([O-])(=O)C.[Na+]>CCO>[CH3:2][CH:3]1[C:8](=[N:13][OH:14])[CH:7]2[CH2:10][CH2:11][N:4]1[CH2:5][CH2:6]2

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 181803571-Azabicyclo[2.2.2]octan-3-one, 2-methyl-, hydrochlorideHCID 23665404Sodium Acetate Trihydrate

Produkt 1

HCID 858099392-Methyl-1-azabicyclo[2.2.2]octan-3-one oximeAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Methylquinuclidin-3-one hydrochloride from Step L (5.3 g, 30.2 mmol, 1 eq), hydroxylamine hydrochloride (2.5 g, 36.4 mmol, 1.2 eq) and sodium acetate trihydrate (12.4 g, 90.9 mmol, 3 eq) are suspended in 70 mL EtOH and stirred at room temperature. After 24 h, the mixture is concentrated in vacuo. The residue is suspended in CHCl3 and the solids are filtered. The solids are rinsed with excess CH3CN. The combined organic washes are concentrated in vacuo to give 4.65 g (100%) of 2-methyl-1-azabicyclo[2.2.2]octan-3-one oxime. MS (ESI) for C8H14N2O m/z 155.2 (M+H)+.

Aufarbeitung

  1. concentrationthe mixture is concentrated in vacuo
  2. filtrationthe solids are filtered
  3. washThe solids are rinsed with excess CH3CN
  4. concentrationThe combined organic washes are concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7d84afb2801d4924a15b79513de2a445
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479510B2

Notizen zur Reaktion

Wird geladen…