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

HRID 742594Notes

Reaction equation

HRID 742594 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. Upon completion of the addition, 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 resulting suspension was filtered through a pad of celite, and the filter cake was washed with dichloromethane. The combined filtrates were dried over anhydrous potassium carbonate, filtered, and the filtrate was concentrated to give 6.3 g (96%) of 2-(3-methoxyphenyl)pyrrolidine.

Workup

  1. customdropwise at ambient temperature
  2. additionUpon completion of the addition
  3. temperaturethe reaction mixture was warmed
  4. temperatureunder reflux for 2 hrs
  5. customquenched with 10% aqueous tetrahydrofuran (60 ml)
  6. filtrationThe resulting suspension was filtered through a pad of celite
  7. washthe filter cake was washed with dichloromethane
  8. dry with materialThe combined filtrates were dried over anhydrous potassium carbonate
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e5b659464ec44a28b42db2fd69241016
Source dataset
uspto-grants-1996_09
Patent number
US05554750

Reaction notes

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