ethyl 3-[N,N'-bis(benzyloxycarbonyl)hydrazino]-2,5-dioxopyrrolidine-3-carboxylate → Ethyl 3-hydrazino-2,5-dioxopyrrolidine-3-carboxylate

HRID 1943006Notes

Reaction equation

HRID 1943006 reaction equation
C(OC([N:11]([C:23]1([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29])[NH:12]C(OCC1C=CC=CC=1)=O)=O)C1C=CC=CC=1.[H][H]>C(O)C>[NH:11]([C:23]1([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29])[NH2:12]

Participants

4

Reactant 2

HCID 58382718ethyl 3-[N,N'-bis(benzyloxycarbonyl)hydrazino]-2,5-dioxopyrrolidine-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 66992301Ethyl 3-hydrazino-2,5-dioxopyrrolidine-3-carboxylateYield 100.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound of Example 1 (1.00 g) in ethanol (30 ml) was added 5% palladium-carbon ethylenediamine complex (100 mg). The mixture was stirred vigorously at room temperature under hydrogen (atmospheric pressure) for 2.5 hours. During this reaction, to remove carbon dioxide generated with the progress of the reaction, the gas in the reactor was replaced with hydrogen gas several times. The reaction mixture was filtered through a Celite pad and then the Celite was washed with ethanol. The filtrate combined with the washers was concentrated to give the desired product (432 mg, quantitative) as oil

Workup

  1. customDuring this reaction
  2. customto remove carbon dioxide
  3. customgenerated with the progress of the reaction
  4. filtrationThe reaction mixture was filtered through a Celite pad
  5. washthe Celite was washed with ethanol
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-d5d7a57e1d6f4563bba70aa529f19825
Source dataset
uspto-grants-2013_03
Patent number
US08389742B2

Reaction notes

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