Ethanol → 4-[4-(4-fluorophenyl)-1-hydroxy-1-(4-tert-butylaminocarbonylphenyl)butyl]-1H-imidazole

HRID 744719Notes

Reaction equation

HRID 744719 reaction equation
C([N:8]1[C:12]([C:13]([OH:37])([C:24]2[CH:29]=[CH:28][C:27]([C:30]([NH:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:26][CH:25]=2)[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:11][N:10]=[CH:9]1)C1C=CC=CC=1.C(O)C.C([O-])=O.[NH4+]>[Pd].O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH2:15][CH2:14][C:13]([C:12]2[N:8]=[CH:9][NH:10][CH:11]=2)([OH:37])[C:24]2[CH:29]=[CH:28][C:27]([C:30]([NH:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])=[CH:26][CH:25]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 194219951-benzyl-5-[4-(4-fluorophenyl)-1-hydroxy-1-(4-tert-butylaminocarbonylphenyl)butyl]-1-H-imidazole

Product 1

HCID 1784493104-[4-(4-fluorophenyl)-1-hydroxy-1-(4-tert-butylaminocarbonylphenyl)butyl]-1H-imidazole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

12,95 g of 1-benzyl-5-[4-(4-fluorophenyl)-1-hydroxy-1-(4-tert-butylaminocarbonylphenyl)butyl]-1-H-imidazole is dissolved into ethanol (400 ml) and water (130 ml). 8,17 g of ammonium formate and 1,3 g of 10% Pd/C is added to the solution and the mixture is refluxed for three hours. Then the reaction mixture is filtered through siliceous earth and the flitrate is evaporated to dryness. The residue is dissolved into ethyl acetate, washed with 2M aqueous sodium hydroxide and water, dried and evaporated to dryness.

Workup

  1. temperaturethe mixture is refluxed for three hours
  2. filtrationThen the reaction mixture is filtered through siliceous earth
  3. customthe flitrate is evaporated to dryness
  4. dissolutionThe residue is dissolved into ethyl acetate
  5. washwashed with 2M aqueous sodium hydroxide and water
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-f491f2ceab98476cbd872f0c8094d752
Source dataset
uspto-grants-1996_09
Patent number
US05559141

Reaction notes

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