Water → 3-(3,4-Dimethoxyphenyl)-3-(2-hydroxyethyl)pyrrolidine

HRID 1682977Notes

Reaction equation

HRID 1682977 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)[CH2:10][C:9](=O)[NH:8][CH2:7]1)C.O.[OH-].[Na+]>C1COCC1.ClCCl>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([C:6]2([CH2:5][CH2:4][OH:3])[CH2:10][CH2:9][NH:8][CH2:7]2)[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

6

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15392020(3-(3,4-Dimethoxyphenyl)-5-oxopyrrolidin-3-yl)acetic acid ethyl ester

Product 1

HCID 153920213-(3,4-Dimethoxyphenyl)-3-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Combined LiA1H4 (4.80 g, 127 mmol, 4 eq) and anhydrous THF (200 mL). Added portionwise, a slurry of [3-(3,4-dimethoxy-phenyl)-5-oxo-pyrrolidin-3-yl]-acetic acid ethyl ester (9.72 g, 31.6 mmol) in THF (100 mL). After the addition was complete, the reaction was heated at reflux overnight. Cooled in an ice/NaCl bath. Cautiously added H2O (4.8 mL), NaOH (4.8 mL, 15%), and H2O (19.2 mL). Filtered. Concentrated the filtrate to obtain a residue. Dissolved the residue in dichloromethane and dried over MgSO4, filtered, and concentrated the filtrate in vacuo to obtain a residue which was dried at 0.05 Torr overnight to give the title compound. This material was used without further purification.

Workup

  1. additionAdded portionwise
  2. additionAfter the addition
  3. temperaturethe reaction was heated
  4. temperatureat reflux overnight
  5. temperatureCooled in an ice/NaCl bath
  6. filtrationFiltered
  7. concentrationConcentrated the filtrate
  8. customto obtain a residue
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated the filtrate in vacuo
  12. customto obtain a residue which
  13. customwas dried at 0.05 Torr overnight

Sources & evidence

ORD record
ord-465389c8e6b54a94a87b560cc60a9e08
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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