Sodium Chloride → 1-Pyrrolidineacetic acid, 4-hydroxy-2-oxo-, (+-)-

HRID 1197670Notes

Reaction equation

HRID 1197670 reaction equation
C[O:2][C:3]1[CH2:7][N:6]([CH2:8][C:9]([OH:11])=[O:10])[C:5](=[O:12])[CH:4]=1.C([O-])(=O)C.[Na+].[Na+].[Cl-]>Cl.[Ru]>[OH:2][CH:3]1[CH2:7][N:6]([CH2:8][C:9]([OH:11])=[O:10])[C:5](=[O:12])[CH2:4]1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 517045Sodium AcetateHCID 10910005HCID 10910005, compound

Product 1

HCID 111265411-Pyrrolidineacetic acid, 4-hydroxy-2-oxo-, (+-)-Yield 60%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
70 °C

Procedure

2.0 g (11.7 mmol) of 4-methoxy-3-pyrrolin-2-on-1-yl-acetic acid was dissolved in 15 ml of HCl (1N) at room temperature and heated to 70° C. with stirring. After 1 hour, 2.04 g of sodium acetate was added to adjust the PH to 2.0. 100 mg of Ru/C was added to the reaction mixture. The reaction mixture was transferred to an autoclave and hydrogenated at 10 bars of H2 pressure with stirring. After 18 hours, the catalyst was filtered off by suction and the filtrate was concentrated by evaporation in a vacuum. The latter yielded 2.9 g of a crude mixture of NaCl and 4-hydroxy-pyrrolidin-2-on-1-yl-acetic acid (42 percent content, 60 percent yield).

Workup

  1. stirringwith stirring
  2. waitAfter 18 hours
  3. filtrationthe catalyst was filtered off by suction
  4. concentrationthe filtrate was concentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-95ccff37d0a447c2a1013ed4c4ecad83
Source dataset
uspto-grants-1994_01
Patent number
US05276164

Reaction notes

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