t-Butyl 2-(4-amino-2-((2'-fluorobiphenyl-4-yl)oxy)-5-nitrophenyl)pyrrolidine-1-carboxylate → t-Butyl 2-(4,5-diamino-2-((2'-fluorobiphenyl-4-yl)oxy)phenyl)pyrrolidine 1-carboxylate

HRID 13401Notes

Reaction equation

HRID 13401 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([CH:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:4]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[F:36])=[CH:26][CH:25]=2)[CH:3]=1.[H][H]>[Ni].CO>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([CH:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])=[C:4]([O:23][C:24]2[CH:25]=[CH:26][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[F:36])=[CH:28][CH:29]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 23145747t-Butyl 2-(4-amino-2-((2'-fluorobiphenyl-4-yl)oxy)-5-nitrophenyl)pyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 23145792t-Butyl 2-(4,5-diamino-2-((2'-fluorobiphenyl-4-yl)oxy)phenyl)pyrrolidine 1-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1 ml of developed Raney nickel was added to a methanol (5 ml) solution of 410 mg of t-butyl 2-(4-amino-2-((2′-fluorobiphenyl-4-yl)oxy)-5-nitrophenyl)pyrrolidine-1-carboxylate, and the reaction liquid was stirred in a hydrogen atmosphere at room temperature for 1 day. The catalyst was removed through filtration through Celite, and the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1) to obtain the entitled compound as a brown oily substance.

Workup

  1. customthe reaction liquid
  2. customThe catalyst was removed through filtration through Celite
  3. customthe solvent was evaporated away under reduced pressure
  4. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1)
  5. customto obtain the entitled compound as a brown oily substance

Sources & evidence

ORD record
ord-3a02d6f248624bc2a1e054512125231a
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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