Ammonium formate → 2-Tert-butyl-4-fluoro-6-aminophenyl methyl carbonate

HRID 1915310Notes

Reaction equation

HRID 1915310 reaction equation
[C:1](=[O:19])([O:17][CH3:18])[O:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([F:12])=[CH:5][C:4]=1[C:13]([CH3:16])([CH3:15])[CH3:14].C([O-])=O.[NH4+]>CCO.[Pd]>[C:1](=[O:19])([O:17][CH3:18])[O:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([F:12])=[CH:5][C:4]=1[C:13]([CH3:14])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 574702172-Tert-butyl-4-fluoro-6-nitrophenyl methyl carbonate

Product 1

HCID 574702262-Tert-butyl-4-fluoro-6-aminophenyl methyl carbonateYield 27%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of 2-tert-butyl-4-fluoro-6-nitrophenyl methyl carbonate (250 mg, 0.92 mmol) and ammonium formate (250 mg, 4 mmol) in EtOH (10 mL) was added 5% Pd—C (170 mg). The mixture was refluxed for additional 1 h, cooled and filtered through Celite. The solvent was removed by evaporation and the residue was purified by column chromatography (0-15%, EtOAc-Hexane) to give 2-tert-butyl-4-fluoro-6-aminophenyl methyl carbonate (C-6) (60 mg, 27%). HPLC ret. time 3.35 min, 10-99% CH3CN, 5 min run; ESI-MS 242.0 m/z (MH+).

Workup

  1. temperatureThe mixture was refluxed for additional 1 h
  2. temperaturecooled
  3. filtrationfiltered through Celite
  4. customThe solvent was removed by evaporation
  5. customthe residue was purified by column chromatography (0-15%, EtOAc-Hexane)

Sources & evidence

ORD record
ord-870f1b4eedd34396abeb8a8b5926b9f0
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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