Ammonium formate → (S)-1-(3-(2-amino-5-methylphenoxy)piperidin-1-yl)-2,2,2-trifluoroethanone

HRID 240601Notes

Reaction equation

HRID 240601 reaction equation
C([O-])=O.[NH4+].[F:5][C:6]([F:27])([F:26])[C:7]([N:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([O:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=2[N+:23]([O-])=O)[CH2:10]1)=[O:8]>[Pd].CO>[NH2:23][C:17]1[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=1[O:15][C@H:11]1[CH2:12][CH2:13][CH2:14][N:9]([C:7](=[O:8])[C:6]([F:27])([F:5])[F:26])[CH2:10]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58413139(S)-2,2,2-trifluoro-1-(3-(5-methyl-2-nitrophenoxy)piperidin-1-yl)ethanone

Product 1

HCID 58413119(S)-1-(3-(2-amino-5-methylphenoxy)piperidin-1-yl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Amoniumformiate (0.238 g) was added into a suspension of (S)-2,2,2-trifluoro-1-(3-(5-methyl-2-nitrophenoxy)piperidin-1-yl)ethanone and palladium on charcoal (50.0 mg) in MeOH (6.0 ml) at room temperature. The mixture was heated at reflux for 40 mins. The mixture was filtered through a pad of celite and the filtercake was washed with dichloromethane. The filtrate was washed with water and. The residue was purfied by chromatography.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 40 mins
  3. filtrationThe mixture was filtered through a pad of celite
  4. washthe filtercake was washed with dichloromethane
  5. washThe filtrate was washed with water

Sources & evidence

ORD record
ord-300843a7813441c6b1ca2abcb34f42f2
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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