HCID 21301011, compound → HCID 21301002, compound

HRID 49975Notes

Reaction equation

HRID 49975 reaction equation
C([N:8]1[CH2:12][CH:11]2[C:13](=[O:25])[N:14]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[C:15](=[O:16])[CH:10]2[CH2:9]1)C1C=CC=CC=1>C(O)(=O)C.[Pt]=O>[Cl:23][C:21]1[CH:22]=[C:17]([N:14]2[C:13](=[O:25])[CH:11]3[CH:10]([CH2:9][NH:8][CH2:12]3)[C:15]2=[O:16])[CH:18]=[C:19]([Cl:24])[CH:20]=1

Participants

4

Reactant 1

HCID 21301011HCID 21301011, compound

Product 1

HCID 21301002HCID 21301002, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 5-benzyl-2-(3,5-dichlorophenyl)-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione (1.13 g, 3 mmol) in acetic acid (20 mL) was hydrogenated at atmospheric pressure over platinum oxide for 4 h. The catalyst was filtered off and the filtrate was poured into an ammonium hydroxide solution. The aqueous solution was extracted twice with methylene chloride. The organic layer was dried over sodium sulfate and concentrated in vacuo to give an oil (0.86 g) which was chromatographed over silica gel (CH2Cl2/MeOH/NH4OH: 90/9/1) to yield the above compound as a white solid (0.53 g). Mp=170° C. 1H NMR (DMSO-d6): 7.73 (1H, m), 7.47 (2H, m), 3.2-3.5 (4H, m), 2.8-2.9 (2H, m).

Workup

  1. filtrationThe catalyst was filtered off
  2. additionthe filtrate was poured into an ammonium hydroxide solution
  3. extractionThe aqueous solution was extracted twice with methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-039c11b45a7d44e1be582eb06aed2cb7
Source dataset
uspto-grants-2004_03
Patent number
US06710064B2

Reaction notes

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