Hydrochloric Acid → 4-(Hydroxymethyl)-1-(4-methylphenyl)-2-pyrrolidinone

HRID 1885622Notes

Reaction equation

HRID 1885622 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([N:7]2[C:11](=[O:12])[CH2:10][CH:9]([C:13](OC)=[O:14])[CH2:8]2)=[CH:3][CH:2]=1.B.[Na].CO.Cl>O1CCCC1.O>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([N:7]2[CH2:8][CH:9]([CH2:13][OH:14])[CH2:10][C:11]2=[O:12])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 577835HCID 577835, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 103529084-(Hydroxymethyl)-1-(4-methylphenyl)-2-pyrrolidinoneYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1-(4-tolyl)-5-oxo-3-pyrrolidinecarboxylate (46.00 g) and sodium boron hydride (5.94 g) are suspended in tetrahydrofuran (460 ml) and to the mixture is added dropwise methanol (46.2 ml) over a period of 1 hour under refluxing. The mixture is further heated for 1 hour. After cooling the reaction mixture, conc. hydrochloric acid (13.7 ml) and water (about 5 ml) are added thereto and then the mixture is concentrated under reduced pressure. Methylene chloride (400 ml) is added to the residue and the insoluble material is removed by filtration. The filtrate is washed with water (about 100 ml). The organic layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the desired product (39.80 g) as solid.

Workup

  1. temperatureunder refluxing
  2. temperatureThe mixture is further heated for 1 hour
  3. additionare added
  4. concentrationthe mixture is concentrated under reduced pressure
  5. additionMethylene chloride (400 ml) is added to the residue
  6. customthe insoluble material is removed by filtration
  7. washThe filtrate is washed with water (about 100 ml)
  8. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c246a7bcbac54672906b80c5286060c1
Source dataset
uspto-grants-1992_09
Patent number
US05145865

Reaction notes

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