Ammonium formate → HCID 69669353, compound

HRID 450578Notes

Reaction equation

HRID 450578 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][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][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][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69669165HCID 69669165, compound

Product 1

HCID 69669353HCID 69669353, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (1.2 g, 19.1 mmol) was added into a suspension of tert-butyl 4-(5-fluoro-2-nitrophenoxy)piperidine-1-carboxylate (2.0 g, 5.8 mmol) and palladium on carbon (5%, 0.4 g) in MeOH (30 mL) at ambient temperature. The solution was stirred for 0.5 hours, filtered through Celite and washed with MeOH. The filtrate was concentrated in vacuo and triturated from diethyl ether to remove the ammonium formate by-products. The sample was purified by flash column chromatography (1:10→1:1 EtOAc/DCM) to yield a colourless oil which crystallised from diethyl ether/petroleum ether (40-60° C.) as a colourless solid (1.6 g, 87%).

Workup

  1. filtrationfiltered through Celite
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. customtriturated from diethyl ether
  5. customto remove the ammonium formate by-products
  6. customThe sample was purified by flash column chromatography (1:10→1:1 EtOAc/DCM)
  7. customto yield a colourless oil which
  8. customcrystallised from diethyl ether/petroleum ether (40-60° C.) as a colourless solid (1.6 g, 87%)

Sources & evidence

ORD record
ord-e9a730ca4f7340dfba5b660736f37004
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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