1,4-Cyclohexadiene → (1R*,2R*,5R*)-1-Phenyl-8-azabicyclo[3.2.1]octan-2-ol

HRID 2088125

Reaktionsgleichung

Reaktionsgleichung von HRID 2088125
C([N:8]1[C@@H:13]2[CH2:14][CH2:15][C@@:9]1([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:10]([OH:16])[CH2:11][CH2:12]2)C1C=CC=CC=1.C1CC=CCC=1>[Pd].O.C(O)C>[C:17]1([C@:9]23[NH:8][C@H:13]([CH2:14][CH2:15]2)[CH2:12][CH2:11][C@H:10]3[OH:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

6

Edukt 2

HCID 123431,4-CyclohexadieneHCID 69688994(1R*,2R*,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

Produkt 1

HCID 69889676(1R*,2R*,5R*)-1-Phenyl-8-azabicyclo[3.2.1]octan-2-olAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

10% Palladium on carbon (4 g) was added as a slurry in water (25 ml) to a solution of (1R*,2R*,5R*)-8-benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol (Description 9; 29.3 g, 100 mmol) and 1,4-cyclohexadiene (80 g, 1 mol) in ethanol (250 ml). The mixture was heated at 60° C. for 6 hours. On cooling to room temperature the mixture was filtered through Celite™ and the filtrate concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5 and 10% methanol/dichloromethane/1% ammonia to yield the title compound (12.2 g, 60%).

Aufarbeitung

  1. temperatureOn cooling to room temperature the mixture
  2. filtrationwas filtered through Celite™
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 5 and 10% methanol/dichloromethane/1% ammonia

Quellen und Nachweise

ORD-Eintrag
ord-db99fa7220d045908dfc64b7b74f3772
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727249B2

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