p-Toluenesulfonic acid → HCID 14881101, compound

HRID 484069Notes

Reaction equation

HRID 484069 reaction equation
[C:1]1([NH:7][C:8]([N:10]2[CH:14]([CH2:15][O:16]C3CCCCO3)[CH2:13][CH2:12][C:11]2=[O:23])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:16][CH2:15][CH:14]1[N:10]([C:8](=[O:9])[NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11](=[O:23])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 19387299HCID 19387299, compound

Product 1

HCID 14881101HCID 14881101, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 1-phenylcarbamoyl-5-(2-tetrahydropyranoxy)methyl-2-pyrrolidinone (7.96 g) was dissolved in 20 ml of methanol, and the solution was stirred at room temperature for 3 hours with addition of 8.6 g of p-toluenesulfonic acid. The solvent was distilled off in a vacuum, 100 ml of water was added to the residue, and the mixture was subjected to extraction with chloroform. The extract was dried over magnesium sulfate and distilled in a vacuum to remove the solvent. The residure was subjected to silica gel column chromatography to obtain an eluate of chloroform/methanol=9/1, which gave 4.86 g of 5-hydroxymethyl-1-phenylcarbamoyl-2-pyrrolidinone (yield 83%) having a melting point of 99° to 101° C.

Workup

  1. distillationThe solvent was distilled off in a vacuum, 100 ml of water
  2. additionwas added to the residue
  3. extractionthe mixture was subjected to extraction with chloroform
  4. dry with materialThe extract was dried over magnesium sulfate
  5. distillationdistilled in a vacuum
  6. customto remove the solvent
  7. customto obtain an eluate of chloroform/methanol=9/1, which

Sources & evidence

ORD record
ord-7318e45d5543465e845aa34d0d4d76c7
Source dataset
uspto-grants-1993_07
Patent number
US05229402

Reaction notes

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