5-(3-Methoxyphenyl)-2-pyrrolidinone → 2-(3-Methoxyphenyl)pyrrolidine

HRID 742573Notes

Reaction equation

HRID 742573 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[NH:13][C:12](=O)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 152932255-(3-Methoxyphenyl)-2-pyrrolidinoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 36138242-(3-Methoxyphenyl)pyrrolidineYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-methoxyphenyl)-2-pyrrolidinone (7.0 g) in dry tetrahydrofuran (280 ml) was added lithium aluminum hydride (55 ml of 1.0M soln.) dropwise at ambient temperature, under nitrogen. The reaction mixture was warmed under reflux for 2 hrs. After cooling to ambient temperature, the reaction was quenched with 10% aqueous tetrahydrofuran (60 ml) followed by 10% sodium hydroxide solution (50 ml). The suspension was filtered through a pad of celite and the filter cake was washed with dichloromethane. The combined filtrates were concentrated. The concentrate was dried over anhydrous potassium carbonate, and filtered. The filtrate was concentrated to give 6.3 g (96%) of 2-(3-methoxyphenyl)pyrrolidine.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureunder reflux for 2 hrs
  3. customthe reaction was quenched with 10% aqueous tetrahydrofuran (60 ml)
  4. filtrationThe suspension was filtered through a pad of celite
  5. washthe filter cake was washed with dichloromethane
  6. concentrationThe combined filtrates were concentrated
  7. dry with materialThe concentrate was dried over anhydrous potassium carbonate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b2f62e0b81964ea08001a653430f702a
Source dataset
uspto-grants-1996_09
Patent number
US05554750

Reaction notes

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