Idramantone → 5-Hydroxy-adamantan-2-one oxime

HRID 1990989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1990989
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=O)[CH2:3]1)[CH2:9]2.Cl.[NH2:14][OH:15]>CCO.[OH-].[Na+]>[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=[N:14][OH:15])[CH2:3]1)[CH2:9]2

Komponenten

5

Edukt 2

HCID 64184IdramantoneHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 230089835-Hydroxy-adamantan-2-one oximeAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5-Hydroxyadmantan-2-one (TCI America, Portland, Oreg.; 3 g, 18.0 mmol) was dissolved in EtOH (20 mL) and the solution was added to a solution of hydroxylamine hydrochloride (12 g, 172.7 mmol) in 1N NaOH (16 mL). The mixture was heated at 100° C. for 1 hour. The EtOH was evaporated, and water and DCM were added. The separated aqueous layer was further extracted twice with DCM. The combined DCM layers were evaporated under vacuum. Crystallization from EtOAc gave 5-hydroxy-adamantan-2-one oxime (2.3 g, 71%).

Aufarbeitung

  1. customThe EtOH was evaporated
  2. additionwater and DCM were added
  3. extractionThe separated aqueous layer was further extracted twice with DCM
  4. customThe combined DCM layers were evaporated under vacuum
  5. customCrystallization from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-fd671fa92bdc40ee886bca327b613883
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645773B2

Notizen zur Reaktion

Wird geladen…