HCID 69954278, compound → HCID 69956475, compound

HRID 2293304Notes

Reaction equation

HRID 2293304 reaction equation
[CH2:1]([N:8]1[C:15](=[O:16])[CH:14]2[CH:10]([CH:11]([CH3:25])[N:12]([CH3:24])[CH:13]2[C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=2)[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cu][C:28]#[N:29]>CN(C=O)C>[CH2:1]([N:8]1[C:9](=[O:26])[CH:10]2[CH:11]([CH3:25])[N:12]([CH3:24])[CH:13]([C:17]3[CH:22]=[CH:21][C:20]([C:28]#[N:29])=[CH:19][CH:18]=3)[CH:14]2[C:15]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69954278HCID 69954278, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 69956475HCID 69956475, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

400 mg (0.96 mmol) of (3aRS,4SR,6RS,6aSR)-2-benzyl-4-(4-bromo-phenyl)-5,6-dimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione and 360 mg (4.02 mmol) of copper(I) cyanide were suspended in 25 ml of DMF and heated under reflux and under argon for 18 hours. After cooling about 15 ml of DMF were removed, then 30 ml of dichloromethane and 20 ml of concentrated aqueous ammonia solution were added. The mixture was stirred vigorously for a few hours. The blue aqueous phase was separated and the organic phase was washed twice with ammonia solution and once with water. The solvent was removed and the residue was purified chromatographically (hexane/ethyl acetate 2:1+1% triethylamine). 293 mg of (1RS,3SR,3aRS,6aSR)-4-(5-benzyl-2,3-dimethyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-yl)-benzonitrile (85%) were isolated as colourless crystals. M.p.: 188°-190° C. (ethyl acetate). FAB-MS: 719 ([2M+H]+, 3); 512 (3); 360 ([M+H]+, 100); 344 (41); 289 (15); 107 (37); 91 (56).

Workup

  1. temperatureheated
  2. temperatureunder reflux and under argon for 18 hours
  3. customwere removed
  4. addition30 ml of dichloromethane and 20 ml of concentrated aqueous ammonia solution were added
  5. customThe blue aqueous phase was separated
  6. washthe organic phase was washed twice with ammonia solution and once with water
  7. customThe solvent was removed
  8. customthe residue was purified chromatographically (hexane/ethyl acetate 2:1+1% triethylamine)

Sources & evidence

ORD record
ord-7045575838b046e5b28f54c5b95d1ea0
Source dataset
uspto-grants-1997_11
Patent number
US05686459

Reaction notes

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