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

HRID 233033Notes

Reaction equation

HRID 233033 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 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-(3-methoxyphenyl)-2-pyrrolidinone (7.0 g) in dry tetrahydrofuran (280 ml) was added 1M lithium aluminum hydride in tetrahydrofuran (55 ml) dropwise at ambient temperature, under nitrogen. The reaction mixture was warmed under reflux for 2 hrs, cooled to ambient temperature, and 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, 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. customquenched 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 materialdried over anhydrous potassium carbonate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e985a0f6c3604debab4c15481a361d52
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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