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

HRID 36668

Reaction equation

HRID 36668 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]pyrroleYield 56%

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)

Sources & evidence

ORD record
ord-f0e21d3541234709a7e0200795083ab8
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Linked notes

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