Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 21265856, compound

HRID 1527266Notes

Reaction equation

HRID 1527266 reaction equation
[CH:1]1[N:2]=[C:3]([CH2:10][C:11]([OH:13])=[O:12])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[C:14]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CO>[CH3:14][O:12][C:11](=[O:13])[CH2:10][C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[CH:1][N:2]=1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 55262594HCID 55262594, compound

Product 1

HCID 21265856HCID 21265856, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of imidazo[1,5-a]pyridin-3-ylacetic acid (Ellanovalabs, 2 g, 11.35 mmol) and camphorsulfonic acid (2.9 g, 12.49 mmol) in MeOH (120 mL) was refluxed for 4 h. Then allowed to cool to RT and concentrated under reduced pressure. The crude residue was diluted in CH2Cl2 and the organic layer was washed with a saturated aqueous solution of NaHCO3. The organics were dried (Na2SO4), filtered and concentrated. The material thus obtained was used in the next step without further purification: TLC, Rf (CH2Cl2/MeOH 9:1)=0.55; MS (UPLC/MS): 191.1 [M+H]+; tR (HPLC conditions f): 0.4 min.

Workup

  1. temperaturewas refluxed for 4 h
  2. concentrationconcentrated under reduced pressure
  3. additionThe crude residue was diluted in CH2Cl2
  4. washthe organic layer was washed with a saturated aqueous solution of NaHCO3
  5. dry with materialThe organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe material thus obtained
  9. customwas used in the next step without further purification
  10. custom0.4 min.

Sources & evidence

ORD record
ord-7e0f640545b045ebaa3929d2bf9f0a96
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…