7-Benzyloxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazole-5-carboxylic Acid Dimethylamide → 7-Hydroxy-2-methyl-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazole-5-carboxylic Acid Dimethylamide

HRID 969539Notes

Reaction equation

HRID 969539 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]([C:5]1[CH:22]=[C:21]([O:23]CC2C=CC=CC=2)[C:8]2[N:9]=[C:10]([CH3:20])[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7]=2[CH:6]=1)=[O:4]>C(O)C.[Pd]>[CH3:31][N:2]([CH3:1])[C:3]([C:5]1[CH:22]=[C:21]([OH:23])[C:8]2[N:9]=[C:10]([CH3:20])[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19])[C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 462211637-Benzyloxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazole-5-carboxylic Acid Dimethylamide

Product 1

HCID 462211647-Hydroxy-2-methyl-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazole-5-carboxylic Acid DimethylamideYield 89.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3.6 g (8.3 mmol) 7-benzyloxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzo-imidazole-5-carboxylic acid dimethylamide in 400 ml ethanol was hydrogenated over 365 mg 10% Pd/C at room temperature for 1 h. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was crystallized from diisopropyl ether to afford 2.6 g (89%) of the title compound as a while solid. m.p. 150°-151° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-3e8c41c3e32e47e9879dbbdde056b145
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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