p-Toluenesulfonic acid → (5S)-5-(Hydroxymethyl)-3,3-dimethylpyrrolidin-2-one

HRID 1619458Notes

Reaction equation

HRID 1619458 reaction equation
CC1(C)[N:6]2[C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH2:9][CH:5]2[CH2:4][O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:3][CH2:4][C@H:5]1[NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH2:9]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66623241HCID 66623241, compound

Product 1

HCID 54023581(5S)-5-(Hydroxymethyl)-3,3-dimethylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 27.15 g I.46 (3,3,6,6-tetramethyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one) and 0.282 g p-toluenesulfonic acid in 500 ml methanol was stirred at reflux overnight. The mixture was concentrated. Additional 500 ml methanol and 2.8 g p-toluenesulfonic acid were added and the mixture was stirred 4 h at reflux. The mixture was diluted with water and treated with sodium carbonate to obtain a basic pH. The organic layer was separated, dried with magnesium sulfate and concentrated to give 1 g (60% content; 3% of theory)

Workup

  1. temperatureat reflux overnight
  2. concentrationThe mixture was concentrated
  3. additionAdditional 500 ml methanol and 2.8 g p-toluenesulfonic acid were added
  4. stirringthe mixture was stirred 4 h
  5. temperatureat reflux
  6. additionThe mixture was diluted with water
  7. additiontreated with sodium carbonate
  8. customto obtain a basic pH
  9. customThe organic layer was separated
  10. dry with materialdried with magnesium sulfate
  11. concentrationconcentrated
  12. customto give 1 g (60% content; 3% of theory)

Sources & evidence

ORD record
ord-ea77c2c9eb9b41fc9f6c1748de399bca
Source dataset
uspto-grants-2014_07
Patent number
US08772305B2

Reaction notes

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