9-(4-Benzyloxy-phenyl)-bicyclo[3.3.1]nonane → 4-(Bicyclo[3.3.1]nonan-9-yl)phenol

HRID 237764Notes

Reaction equation

HRID 237764 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH:20]3[CH2:21][CH2:22][CH2:23][CH:16]2[CH2:17][CH2:18][CH2:19]3)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.CCOC(C)=O.[Pd]>[CH:16]12[CH:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[CH:20]([CH2:19][CH2:18][CH2:17]1)[CH2:21][CH2:22][CH2:23]2

Participants

5

Reactant 1

HCID 685293519-(4-Benzyloxy-phenyl)-bicyclo[3.3.1]nonane

Product 1

HCID 443594624-(Bicyclo[3.3.1]nonan-9-yl)phenol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 9-(4-benzyloxy-phenyl)-bicyclo[3.3.1]nonane (4.4 g, 14.6 mmol) in MeOH (100 mL) and EtOAc (100 mL) (warmed to 40° C. to facilitate dissolution, then cooled to room temperature) was added 10% Pd/C (0.5 g) under N2. This mixture was stirred under H2 (1 atm) overnight. The reaction mixture was then filtered through celite. The filtrate was concentrated to give the title compound as a solid.(3.1 g).

Workup

  1. dissolutiondissolution
  2. filtrationThe reaction mixture was then filtered through celite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f25c2a0e02e045c7a9694e2723a382da
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

Loading…