Water → HCID 18182228, compound

HRID 1359373Notes

Reaction equation

HRID 1359373 reaction equation
[CH2:1]([C:8]1[C:13]([O:14]COC)=[CH:12][CH:11]=[C:10]([N:18]2[CH2:22][CH2:21][C@H:20]([OH:23])[C:19]2=[O:24])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][CH:26]([OH:28])C.O>CC(C)=O>[CH2:1]([C:8]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]([N:18]2[CH2:22][CH2:21][C:20]3([O:23][CH2:25][CH2:26][O:28]3)[C:19]2=[O:24])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3776IsopropanolHCID 21350207HCID 21350207, compound

Product 1

HCID 18182228HCID 18182228, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.1 g of 2-benzyl-3-methoxymethyloxy-6-[(3S)-3-hydroxy-2-pyrrolidinone-1-yl]pyridine was dissolved in 20 ml of acetone, and 1 ml of a Jone's reagent was added thereto, followed by stirring at room temperature for 1.5 hours. 2-Propanol and water were added thereto, followed by extracting with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The resulting residue was dissolved in 20 ml of toluene. 1 ml of ethylene glycol and 198 mg of p-toluenesulfonic acid were added thereto, followed by heating under reflux for 2 hours while removing water by use of Dean Stark apparatus. After cooling as it was, water was added thereto and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 30-40% ethyl acetate/hexane as an eluent for separation and purification, to give 398 mg of the target compound.

Workup

  1. addition1 ml of a Jone's reagent was added
  2. extractionby extracting with ethyl acetate
  3. washThe organic phase was further washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed
  6. dissolutionThe resulting residue was dissolved in 20 ml of toluene
  7. addition1 ml of ethylene glycol and 198 mg of p-toluenesulfonic acid were added
  8. temperatureby heating
  9. temperatureunder reflux for 2 hours
  10. customwhile removing water by use of Dean Stark apparatus
  11. temperatureAfter cooling as it
  12. additionwater was added
  13. extractionthe mixture was extracted with ethyl acetate
  14. washThe organic phase was further washed with brine
  15. dry with materialdried over anhydrous sodium sulfate
  16. customthe solvent was removed
  17. customfor separation and purification

Sources & evidence

ORD record
ord-e200fa8319c94bb5bf0fde6730bfc62a
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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