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

HRID 744724Notes

Reaction equation

HRID 744724 reaction equation
Cl.C([N:9]1[C:13]([C:14]([OH:38])([C:25]2[CH:30]=[CH:29][C:28]([C:31]([NH:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:27][CH:26]=2)[CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:12][N:11]=[CH:10]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][CH2:15][C:14]([C:13]2[N:9]=[CH:10][NH:11][CH:12]=2)([OH:38])[C:25]2[CH:30]=[CH:29][C:28]([C:31]([NH:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])=[CH:27][CH:26]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 194220141-benzyl-5-[4-(4-fluorophenyl)-1-hydroxy-1-(4-tert-butylaminocarbonylphenyl)butyl]-1H-imidazole hydrochloride

Product 1

HCID 1784493104-[4-(4-fluorophenyl)-1-hydroxy-1-(4-tert-butylaminocarbonylphenyl)butyl]-1H-imidazoleYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-benzyl-5-[4-(4-fluorophenyl)-1-hydroxy-1-(4-tert-butylaminocarbonylphenyl)butyl]-1H-imidazole hydrochloride (12,95 g) is dissolved into aqueous ethanol (400 ml) and 1,3 g of 10% Pd/C is added. Ammonium formate (8,17 g) is added to the boiling solution in small portions. The mixture is refluxed for three hours. Then the reaction mixture is filtered through siliceous earth and the filtrate is evaporated to dryness. The residue is dissolved to methylene chloride, washed with 2M sodiumhydroxide and water, dried and evaporated to dryness. Yield 79%.

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed for three hours
  3. filtrationThen the reaction mixture is filtered through siliceous earth
  4. customthe filtrate is evaporated to dryness
  5. dissolutionThe residue is dissolved to methylene chloride
  6. washwashed with 2M sodiumhydroxide and water
  7. customdried
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-c16b678e3e844f2f9de1b75692c34f48
Source dataset
uspto-grants-1996_09
Patent number
US05559141

Reaction notes

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