Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 1-(Tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylic acid

HRID 475085Notes

Reaction equation

HRID 475085 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.C[C:14]1(C)[C:18]2(CS(O)(=O)=O)[C:19](C[CH:15]1[CH2:16]C2)=[O:20]>C1COCC1.O1C=CCCC1>[O:20]1[CH2:19][CH2:18][CH2:14][CH2:15][CH:16]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 2

HCID 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 1,414.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80803,4-dihydro-2H-pyranSolvent

Procedure

To a solution of 1H-benzo[d]imidazole-5-carboxylic acid (1.62 g, 10 mmol) in THF (20 mL), 3,4-dihydro-2H-pyran (2 mL) and CSA (100 mg) were added. The mixture was heated at reflux for 24 h under argon. Removal of solvent followed by SiO2 chromatography afforded 1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carboxylic acid as a light red solid (1.5 g, 60% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h under argon
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-862506f5a6df43828a63dc48d3ecd2db
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

Loading…