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

HRID 1470971Notes

Reaction equation

HRID 1470971 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-179e53665d9c43e58a93e42ca4616315
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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