Carbon Dioxide → (5S)-5-(2-Methylpropyl)pyrrolidine-2,4-dione

HRID 346303Notes

Reaction equation

HRID 346303 reaction equation
[OH:1][C:2]1[C@H:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH:5][C:4](=[O:11])[C:3]=1C(OCC)=O.C(O)C.O.C(=O)=O.[Cl-].[Na+]>C(OCC)(=O)C>[CH3:9][CH:8]([CH3:10])[CH2:7][C@@H:6]1[NH:5][C:4](=[O:11])[CH2:3][C:2]1=[O:1]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 5234Sodium ChlorideHCID 19096565Water ethanolHCID 86743472HCID 86743472, compound

Product 1

HCID 14651688(5S)-5-(2-Methylpropyl)pyrrolidine-2,4-dioneYield 68.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Approximately 150 mmol of (S)-2,5-dihydro-4-hydroxy-5-(2-methylpropyl)-2-oxo-1H-pyrrole-3-carboxylic acid, ethyl ester is added as rapidly as possible to 1 L of boiling ethanol-water (1:1, pot temperature 85-87° C.) in a 3 L beaker with vigorous stirring. Complete solution occurs rapidly and vigorous effervescence is observed. Refluxing is continued 20 minutes until the CO2 evolution ceases. The beaker is plunged into an ice bath to rapidly cool the solution, 120 g of sodium chloride and 500 ml of ethyl acetate are added and the organic layer is separated. The aqueous layer is extracted with 2×500 ml of ethyl acetate and the organic fractions combined, dried over magnesium sulfate and evaporated to a solid. The solid is slurried in 200 ml of diethyl ether, diluted with 200 ml of ethyl acetate, and stirred approximately 15 minutes until most of the solid dissolves. The insoluble material is filtered off and the filtrate evaporated to afford 15.9 g of (S)-5-(2-methylpropyl)-2,4-pyrrolidinedione as an off-white solid; mp 94°-95° C. [α]D23 =-80° (C=1%, chloroform). TLC (ethyl acetate, silica gel, ultra violet (uv)) Rf =0.4.

Workup

  1. temperatureRefluxing
  2. customThe beaker is plunged into an ice bath
  3. additionare added
  4. customthe organic layer is separated
  5. extractionThe aqueous layer is extracted with 2×500 ml of ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to a solid
  8. additiondiluted with 200 ml of ethyl acetate
  9. dissolutiondissolves
  10. filtrationThe insoluble material is filtered off
  11. customthe filtrate evaporated

Sources & evidence

ORD record
ord-580cd044127440dc8dbc19286411436b
Source dataset
uspto-grants-1991_10
Patent number
US05061808

Reaction notes

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