tert-Butyl 2-(5-fluoro-2-nitrophenoxy)propylcarbamate → tert-Butyl 2-(2-amino-5-fluorophenoxy)propylcarbamate

HRID 532256Notes

Reaction equation

HRID 532256 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-])=O)=[C:6]([CH:19]=1)[O:7][CH:8]([CH3:18])[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14]>CO.[Pd]>[NH2:20][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:19][C:6]=1[O:7][CH:8]([CH3:18])[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]

Participants

4

Reactant 1

HCID 58413346tert-Butyl 2-(5-fluoro-2-nitrophenoxy)propylcarbamate

Product 1

HCID 58413393tert-Butyl 2-(2-amino-5-fluorophenoxy)propylcarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 2-(5-fluoro-2-nitrophenoxy)propylcarbamate (3.1 g) in MeOH (5 ml) was added 10% palladium on carbon (300 mg) and the reaction mixture was hydrogenated at room temperature at 50 psi. The catalyst was filtered off and the filtrate was concentrated in vacuo.

Workup

  1. customwas hydrogenated at room temperature at 50 psi
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-be0d9773c66443df96f624b4727ffac0
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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