3,4-dihydro-2H-pyran → 1-(Tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylic acid

HRID 475234Notes

Reaction equation

HRID 475234 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1COCC1>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 178524171HCID 178524171, compound

Product 1

HCID 712724931-(Tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylic acidYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 1H-benzoimidazole-5-carboxylic acid (1.62 g, 10 mmol) in THF (20 mL) was added 3,4-dihydro-2H-pyran (2 mL) and camphorsulfonic acid (100 mg, 0.42 mmol, 0.04 equiv). The mixture was refluxed for 24 h under argon. Concentration and chromatography afforded 1.5 g (60%) of 1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carboxylic acid (166) as a light red solid.

Workup

  1. temperatureThe mixture was refluxed for 24 h under argon
  2. concentrationConcentration and chromatography

Sources & evidence

ORD record
ord-7e715e7f64ca4de9b17816c1007d03c8
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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