1-(4-Chlorophenyl)-2,5-bis(4-nitrophenyl)pyrrolidine → 4,4'-(trans-1-(4-Chlorophenyl)pyrrolidine-2,5-diyl)dianiline

HRID 2364822Notes

Reaction equation

HRID 2364822 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[CH2:11][CH2:10][CH:9]2[C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1>CCO.C1COCC1.[Pt](=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[CH2:11][CH2:10][C@@H:9]2[C:22]2[CH:23]=[CH:24][C:25]([NH2:28])=[CH:26][CH:27]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 866491061-(4-Chlorophenyl)-2,5-bis(4-nitrophenyl)pyrrolidine

Product 1

HCID 672364654,4'-(trans-1-(4-Chlorophenyl)pyrrolidine-2,5-diyl)dianiline

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of example 85A (0.214 g, 0.505 mmol) in EtOH (2.52 mL) and THF (2.52 mL) was added platinum(IV) oxide (0.115 g, 0.505 mmol), and the resulting mixture was stirred at rt under 1 atm H2 overnight. The mixture was filtered through celite, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-12% EtOAc in hexane to give a mixture of the title compound and some dechlorinated product (4,4′-(trans-1-phenylpyrrolidine-2,5-diyl)dianiline).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-12% EtOAc in hexane
  4. customto give

Sources & evidence

ORD record
ord-c516bea4eec04872a34ecd6a43c2d5f0
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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