Ammonium formate → (R)-tert-butyl 3-(2-amino-5-fluorophenoxy)piperidine-1-carboxylate

HRID 240595Notes

Reaction equation

HRID 240595 reaction equation
C([O-])=O.[NH4+].[F:5][C:6]1[CH:7]=[CH:8][C:9]([N+:26]([O-])=O)=[C:10]([CH:25]=1)[O:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]1>[Pd].CO>[NH2:26][C:9]1[CH:8]=[CH:7][C:6]([F:5])=[CH:25][C:10]=1[O:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:13]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67395513(R)-tert-butyl 3-(5-fluoro-2-nitrophenoxy)piperidine-1-carboxylate

Product 1

HCID 58413198(R)-tert-butyl 3-(2-amino-5-fluorophenoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Amoniumformiate (1.0 g) was added into a suspension of (R)-tert-butyl 3-(5-fluoro-2-nitrophenoxy)piperidine-1-carboxylate and palladium on charcoal (125.0 mg) in anhydrous MeOH (10.0 ml) at room temperature. The reaction was stirred at room temperature overnight when LCMS analysis indicated consumption of the starting material. The solution was filtered through celite and washed with MeOH. The filtrate was concentrated in vacuo. The residue was triturated with diethylether to remove the ammoniumformiate residues. The solution was filtered and concentrated in vacuo. The residue was purified by chromatography.

Workup

  1. customconsumption of the starting material
  2. filtrationThe solution was filtered through celite
  3. washwashed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was triturated with diethylether
  6. customto remove the ammoniumformiate residues
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-250dd16659d04b508156aa1c00a196e2
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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