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

HRID 1359661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359661
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.[OH-].[Na+]>CCO.N1C=CC=CC=1>[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

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 181803571-Azabicyclo[2.2.2]octan-3-one, 2-methyl-, hydrochloride

Produkt 1

HCID 858099392-Methyl-1-azabicyclo[2.2.2]octan-3-one oximeAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21975839Pyridine ethanolLösungsmittel

Versuchsvorschrift

The product from Step 158b (3.2 g, 23.0 mmol, 1 eq) and hydroxylamine hydrochloride (1.6 g, 23.0 mmol, 1 eq) are dissolved in 20 mL EtOH/pyridine (4:1) and stirred at room temperature. After 5 days, water and solid NaOH are added to adjust pH to pH 11. The mixture is extracted with several portions of CHCl3. The combined organic layers are dried over MgSO4, filtered and concentrated to give 3.42 g (96%) of 2-methyl-1-azabicyclo[2.2.2]octan-3-one oxime as a 1:2.6 mixture of oxime isomers. Partial 1NMR (CDCl3, 300 MHz) δ 1.53 ppm (d, 2-CH3, 0.8H), 1.38 (d, 2-CH3. 2.2H). MS (ESI) for C8H14N2O m/z 154.8 (M+H)+.

Aufarbeitung

  1. extractionThe mixture is extracted with several portions of CHCl3
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5fbb0d08c76e4659a4818a4561c31b70
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599916B2

Notizen zur Reaktion

Wird geladen…