Formaldehyde → 2,5-Dibenzyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione

HRID 2115277Notes

Reaction equation

HRID 2115277 reaction equation
C=O.[CH2:3]([N:10]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]1=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[CH2:18]([NH:25][CH2:26][C:27](O)=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1(C)C=CC=CC=1>[CH2:3]([N:10]1[C:14](=[O:15])[CH:27]2[CH:12]([CH2:13][N:25]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:26]2)[C:11]1=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 74204BenzylmaleimideHCID 2756624N-Benzylglycine Hydrochloride

Product 1

HCID 218676822,5-Dibenzyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of paraformaldehyde (3.37 g), N-benzylmaleimide (2.80 g) and N-benzylglycine hydrochloride (3.02 g) in toluene (100 mL) was heated to reflux with azeotropic removal of water for 16 hours. The mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by flash chromatography (20% EtOAc/hexane) to afford the title compound 1 as a low melting white solid (3.60 g, 75%). LCMS: Rf: 2.616 min, M+H+: 321.

Workup

  1. temperaturewas heated
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-a83cfb5c8fcb47b0b96e87cdd29a9bc2
Source dataset
uspto-grants-2008_10
Patent number
US07435830B2

Reaction notes

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