Methyl 4-(Benzyloxy)-1-Boc-2-methyl-1H-benzo[d]imidazole-6-carboxylate → Methyl 1-Boc-4-hydroxy-2-methyl-1H-benzo[d]imidazole-6-carboxylate

HRID 2239306Notes

Reaction equation

HRID 2239306 reaction equation
[CH3:1][C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:5]2[CH:14]=[C:15]([C:26]([O:28][CH3:29])=[O:27])[CH:16]=[C:17]([O:18]CC3C=CC=CC=3)[C:4]=2[N:3]=1>O1CCCC1.[OH-].[Pd+2].[OH-]>[OH:18][C:17]1[C:4]2[N:3]=[C:2]([CH3:1])[N:6]([C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8])[C:5]=2[CH:14]=[C:15]([C:26]([O:28][CH3:29])=[O:27])[CH:16]=1

Participants

4

Reactant 1

HCID 68575059Methyl 4-(Benzyloxy)-1-Boc-2-methyl-1H-benzo[d]imidazole-6-carboxylate

Product 1

HCID 68577057Methyl 1-Boc-4-hydroxy-2-methyl-1H-benzo[d]imidazole-6-carboxylateYield 32.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(1,1-dimethylethyl) 6-methyl 2-methyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-1,6-dicarboxylate (12.1 g, crude, STEP 2) and 20% palladium hydroxide (6.0 g) in tetrahydrofuran (250 mL) was stirred under hydrogen gas for 2 hours. The resulted mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuum. The residue was washed with hexane/diethyl ether (10:1) to give the title compound as a white solid (3.02 g, 28% for 3 steps).

Workup

  1. filtrationThe resulted mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuum
  3. washThe residue was washed with hexane/diethyl ether (10:1)

Sources & evidence

ORD record
ord-983ed950aee946989dc67ea07c831595
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

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