Ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-oxopentanoate → 3,3,5-Trimethylpyrrolidine-2,4-dione

HRID 1967229Notes

Reaction equation

HRID 1967229 reaction equation
C(OC([NH:11][CH:12]([CH3:23])[C:13](=[O:22])[C:14]([CH3:21])([CH3:20])[C:15](OCC)=[O:16])=O)C1C=CC=CC=1>CO.[C].[Pd]>[CH3:20][C:14]1([CH3:21])[C:13](=[O:22])[CH:12]([CH3:23])[NH:11][C:15]1=[O:16]

Participants

4

Reactant 1

HCID 59556975Ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-oxopentanoate

Product 1

HCID 552998933,3,5-Trimethylpyrrolidine-2,4-dioneYield 87%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-oxopentanoate (10.5 g) in methanol (150 mL) was added 10% palladium carbon (containing 50% water, 5.0 g), and the mixture was stirred under a hydrogen atmosphere overnight. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The obtained solid was washed with hexane to give the title compound as a colorless solid (yield: 4.00 g, 87%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-bf1ba16109e44e7d81ed2a8827904d55
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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