Ethyl Acetate → HCID 11820478, compound

HRID 1885628Notes

Reaction equation

HRID 1885628 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18](=O)[CH2:17][CH:16]([C:20](O)=[O:21])[CH2:15]2)=[CH:10][CH:9]=1.C(OCC)(=O)C.[OH-].[Na+]>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:18][CH2:17][CH:16]([CH2:20][OH:21])[CH2:15]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2177851-(4-Chlorophenyl)-5-oxopyrrolidine-3-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11820478HCID 11820478, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (2.93 g) is suspended in THF (90 ml) under ice-cooling and thereto is added 1-(4-chlorophenyl)-5-oxo-3-pyrrolidinecarboxylic acid (4.63 g) in portions. The mixture is stirred under refluxing for 20 hours. Ethyl acetate and a small amount of 1N aqueous sodium hydroxide solution are added to the reaction mixture to decompose the excess reducing agent. The mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is subjected to silica gel column chromatography and eluted with a mixed solvent of chloroform/methanol [40:1 (v/v)]to give the desired product (4.00 g).

Workup

  1. temperaturecooling
  2. temperatureunder refluxing for 20 hours
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. washeluted with a mixed solvent of chloroform/methanol [40:1 (v/v)]to

Sources & evidence

ORD record
ord-04b36bcfe8b5483ab7abc23ad21f836c
Source dataset
uspto-grants-1992_09
Patent number
US05145865

Reaction notes

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