tert-Butyl 2-[4-(2-butyl-4-chloro-5-formyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentylacetate → tert-Butyl 2-[4-(2-butyl-5-formyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentyl-acetate

HRID 1955739Notes

Reaction equation

HRID 1955739 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:16][CH:15]=2)[C:7]([CH:11]=[O:12])=[C:8](Cl)[N:9]=1)[CH2:2][CH2:3][CH3:4].[H][H].O.O.O.C([O-])(=O)C.[Na+]>CO.[Pd]>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH:20]([CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:18][CH:19]=2)[C:7]([CH:11]=[O:12])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 15225591tert-Butyl 2-[4-(2-butyl-4-chloro-5-formyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentylacetateHCID 23665404Sodium Acetate TrihydrateHCID 178418361HCID 178418361, compound

Product 1

HCID 19072508tert-Butyl 2-[4-(2-butyl-5-formyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentyl-acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 21.8 g (47.5 mmol) of tert-butyl 2-[4-(2-butyl-4-chloro-5-formyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentyl-acetate in 200 ml of methanol is hydrogenated at a hydrogen pressure of about 2 bar for 1 h at 25° C. in the presence of 2.18 g of palladium on active carbon (5% strength) and 6.47 g (47.5 mmol) of sodium acetate trihydrate. The solution is then filtered off from the catalyst and concentrated, and the residue is chromatographed on silica gel 60 using ethyl acetate/petroleum ether (1:1).

Workup

  1. filtrationThe solution is then filtered off from the catalyst
  2. concentrationconcentrated
  3. customthe residue is chromatographed on silica gel 60 using ethyl acetate/petroleum ether (1:1)

Sources & evidence

ORD record
ord-dc115967a2984c98b555ef57d44b1825
Source dataset
uspto-grants-1998_07
Patent number
US05776964

Reaction notes

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