Sodium hydride → 5-Benzyl-4,6-dioxo-octahydropyrrolo[3,4-b]pyrrole

HRID 974900

Reaction equation

HRID 974900 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:14](=[O:15])[CH2:13][CH:12]([NH:16][CH2:17][CH2:18]Cl)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CN(C)C=O>[CH2:3]([N:10]1[C:14](=[O:15])[CH:13]2[CH:12]([NH:16][CH2:17][CH2:18]2)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 150700021-Benzyl-3-(2-chloroethylamino)pyrrolidine-2,5-dione

Product 1

HCID 150700035-Benzyl-4,6-dioxo-octahydropyrrolo[3,4-b]pyrrole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17.4 g (0.58 mmol) of sodium hydride suspension are reacted with 119 g (0.45 mol) of 1-benzyl-3-(2-chloroethylamino)-pyrrolidine-2,5-dione in 550 ml of absolute dimethylformamide in accordance with the working instructions of Example Ib. After the mixture has been left to stand overnight, it is worked up under aqueous conditions. On purification by chromatography, impurities are first eluted with ethyl acetate and the product is then eluted with ethyl acetate:methanol (3:1) (RF value 0.55) 57.7 g of product (56% of theory) are isolated.

Workup

  1. waitAfter the mixture has been left
  2. customOn purification by chromatography, impurities
  3. washare first eluted with ethyl acetate
  4. washthe product is then eluted with ethyl acetate:methanol (3:1) (RF value 0.55) 57.7 g of product (56% of theory)
  5. customare isolated

Sources & evidence

ORD record
ord-e47393a494a84f7d8f4150c2938ab881
Source dataset
uspto-grants-1997_03
Patent number
US05607942

Linked notes

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