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

HRID 1654023Notes

Reaction equation

HRID 1654023 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 21 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 dichloromcthane. The combined filtrates were dried over anhydrous potassium carbonate, filtered, and concentrated to give 6.3 g (96%) of 2-(3-methoxyphenyl)pyrrolidine.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureunder reflux for 21 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 dichloromcthane
  6. dry with materialThe combined filtrates were dried over anhydrous potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9b353cd33baf4ac6995c7632ddedac9a
Source dataset
uspto-grants-1995_04
Patent number
US05405845

Reaction notes

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