Acetone → (3aRS,4RS,6aSR)-2-benzyl-4-(4-bromo-benzyl)-6,6-dimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione

HRID 2293299Notes

Reaction equation

HRID 2293299 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][C@@H:7](C(O)=O)[NH2:8])=[CH:4][CH:3]=1.[CH3:14][C:15]([CH3:17])=O.[CH2:18]([N:25]1[C:29](=[O:30])[CH:28]=[CH:27][C:26]1=[O:31])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH2:18]([N:25]1[C:29](=[O:30])[CH:28]2[CH:27]([C:15]([CH3:17])([CH3:14])[NH:8][CH:7]2[CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:13][CH:12]=2)[C:26]1=[O:31])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 74204BenzylmaleimideHCID 6712144-Bromo-L-phenylalanine

Product 1

HCID 69952519(3aRS,4RS,6aSR)-2-benzyl-4-(4-bromo-benzyl)-6,6-dimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dioneYield 25.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8.83 g (36.2 mmol) of 4-bromophenylalanine, 4.74 g (81.7 mmol) acetone and 7.00 g (37.43 mmol) of N-benzylmaleimide were heated under reflux for 68 hours. in 140 ml of toluene with the addition of molecular sieve A4. The solvent was removed in a vacuum and the residue was separated chromatographically (hexane/ethyl acetate 1:1+1% triethylamine). As the main product there were obtained 3.88 g of (3aRS,4RS,6aSR)-2-benzyl-4-(4-bromo-benzyl)-6,6-dimethyl-tetrahydro-pyrrolo[3,4-c]pyrrol-1,3-dione as a colourless oil which, after the addition of a small amount of methanol, crystallized overnight to colourless needles. M.p.: 142°-143° C. FAB-MS: 427 ([M+H]+, 58); 257 (66); 240 (8); 200 (6); 91 (58). 2.12 g of (3aRS,4SR,6aSR)-2-benzyl-4-(4-bromobenzyl)-6,6-dimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione were obtained as a byproduct as a colourless oil. FAB-MS: 427 ([M+H]+, 88); 257 (89); 91 (100).

Workup

  1. temperatureunder reflux for 68 hours
  2. customThe solvent was removed in a vacuum
  3. customthe residue was separated chromatographically (hexane/ethyl acetate 1:1+1% triethylamine)

Sources & evidence

ORD record
ord-cd56c4d6d9b84320af368ae2374a1153
Source dataset
uspto-grants-1997_11
Patent number
US05686459

Reaction notes

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