Water → 2-(4-methoxyphenyl)pyrrolidine

HRID 1742237Notes

Reaction equation

HRID 1742237 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[NH:19][C:18](=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.[OH-].[Na+]>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH2:16][CH2:17][CH2:18][NH:19]2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 24436Sodium SulfateHCID 14471837HCID 14471837, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 37569572-(4-methoxyphenyl)pyrrolidineYield 96%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of lithium aluminum hydride (2.26 g) and tetrahydrofuran (185 ml) was added 5-(4-methoxyphenyl)pyrrolidin-2-one in tetrahydrofuran (250 ml). The mixture was heated under reflux for 6 hrs, cooled to ambient temperature, and water (2.5 ml) in tetrahydrofuran and 15% aqueous sodium hydroxide solution (2.5 ml) were added slowly. Additional water (8.5 ml) was added. The suspension was stirred over anhydrous sodium sulfate, filtered through a pad of celite, and the filter cake was washed with tetrahydrofuran. The filtrate was concentrated to give 6.74 g, (96.0%) of 2-(4-methoxyphenyl)pyrrolidine.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hrs
  3. filtrationfiltered through a pad of celite
  4. washthe filter cake was washed with tetrahydrofuran
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9387f8b582194fdab4ff1d7b9722bfe4
Source dataset
uspto-grants-1994_08
Patent number
US05338739

Reaction notes

Loading…