Methyl 7-(benzyloxy)-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carboxylate → Methyl 7-hydroxy-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carboxylate

HRID 1258457Notes

Reaction equation

HRID 1258457 reaction equation
C([O:8][C:9]1[C:14]2[N:15]([CH2:19][CH2:20][O:21][CH3:22])[C:16]([CH3:18])=[N:17][C:13]=2[CH:12]=[C:11]([C:23]([O:25][CH3:26])=[O:24])[CH:10]=1)C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[C:14]2[N:15]([CH2:19][CH2:20][O:21][CH3:22])[C:16]([CH3:18])=[N:17][C:13]=2[CH:12]=[C:11]([C:23]([O:25][CH3:26])=[O:24])[CH:10]=1

Participants

4

Reactant 1

HCID 67220498Methyl 7-(benzyloxy)-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carboxylate

Product 1

HCID 67219571Methyl 7-hydroxy-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carboxylateYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 7-(benzyloxy)-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carboxylate (9.21 g, 26.0 mmol, Step 6) and 10% palladium on carbon (500 mg) in methanol (150 mL) was stirred under hydrogen gas (4 atm) for 5 hours. The resulting mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuo. The residue was suspended in diisopropyl ether (150 mL), and the precipitate was collected by filtration to afford the title compound as a gray solid (6.35 g, 92%).

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-7b6d444a95264b2f8c374e27d5f80084
Source dataset
uspto-grants-2013_06
Patent number
US08466166B2

Reaction notes

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