(+)-(4R)-1-Acetyl-4-acetylthio-2-pyrrolidone → (4R)-4-acetylthio-2-pyrrolidone

HRID 21735Notes

Reaction equation

HRID 21735 reaction equation
C([N:4]1[CH2:8][C@H:7]([C:9](=[O:11])[CH3:10])[CH2:6][C:5]1=[S:12])(=O)C>Cl.CO>[C:9]([C@H:7]1[CH2:8][NH:4][C:5](=[S:12])[CH2:6]1)(=[O:11])[CH3:10]

Participants

3

Reactant 1

HCID 86748734(+)-(4R)-1-Acetyl-4-acetylthio-2-pyrrolidone

Product 1

HCID 86748733(4R)-4-acetylthio-2-pyrrolidoneYield 81.9%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

(+)-(4R)-1-Acetyl-4-acetylthio-2-pyrrolidone (6 g) is dissolved in 5% hydrogen chloride-methanol solution, and the mixture is stirred at room temperature for 25 minutes. The mixture is evaporated to remove the solvent, and the residue is subjected to azeotropic distillation with toluene. To the residue is added acetyl chloride (6 ml), and the mixture is stirred for 4.5 hours. The precipitated crystals are collected by filtration, and dissolved in chloroform. The chloroform solution is washed with water, dried, and evaporated to remove the solvent to give (4R)-4-acetylthio-2-pyrrolidone (3.8 g).

Workup

  1. customThe mixture is evaporated
  2. customto remove the solvent
  3. distillationthe residue is subjected to azeotropic distillation with toluene
  4. additionTo the residue is added acetyl chloride (6 ml)
  5. stirringthe mixture is stirred for 4.5 hours
  6. filtrationThe precipitated crystals are collected by filtration
  7. dissolutiondissolved in chloroform
  8. washThe chloroform solution is washed with water
  9. customdried
  10. customevaporated
  11. customto remove the solvent

Sources & evidence

ORD record
ord-470290baf1994730af836ca7a67e3583
Source dataset
uspto-grants-1995_06
Patent number
US05424446

Reaction notes

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