5-Hydroxy-adamantan-2-one oxime → 4-Aminoadamantan-1-ol

HRID 12817

Reaktionsgleichung

Reaktionsgleichung von HRID 12817
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=[N:12]O)[CH2:3]1)[CH2:9]2.[H][H]>CCO.[Rh]>[NH2:12][CH:5]1[CH:6]2[CH2:11][C:2]3([OH:1])[CH2:9][CH:8]([CH2:10][CH:4]1[CH2:3]3)[CH2:7]2

Komponenten

5

Edukt 2

HCID 230089835-Hydroxy-adamantan-2-one oximeHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 28574474-Aminoadamantan-1-olAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23948RhodiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Rh/Al2O3 (2.3 g, 5 wt. %, 1.1 mmol) was added to a mixture of 5-hydroxy-admantane-2-one oxime (10 g, 55 mmol) in EtOH (100 mL) in a Parr hydrogenation bottle. The hydrogenation reaction was performed in a Parr hydrogenation instrument at 55 psi pressure of hydrogen at 50° C. for 48 hours. The disappearance of starting material and generation of the product were detected by LC-MS. The mixture was filtered through celite and concentrated under vacuum to dryness to give 4-amino-adamantan-1-ol (about 9 g, ˜98%) which was used for the next step without further purification. Mass spectrum: m/z: 168.1 (M+1).

Aufarbeitung

  1. customThe hydrogenation reaction
  2. filtrationThe mixture was filtered through celite
  3. concentrationconcentrated under vacuum to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1ad0844398d448ee9f15db0e50fe4796
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728029B2

Verknüpfte Notizen

Wird geladen…