Ammonium formate → HCID 53641593, compound

HRID 1016078Notes

Reaction equation

HRID 1016078 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([CH2:18][F:19])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.C(OCC)(=O)C.[Pd]>[F:19][CH2:18][C:10]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 54443836HCID 54443836, compound

Product 1

HCID 53641593HCID 53641593, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.27 g (4.8 mmol) of ethyl 1-benzyl-3-(fluoromethyl)pyrrolidine-3-carboxylate in 20 mL of methanol was added 500 mg of Pd/C (10% on carbon) and 1.5 g (24 mmol) of HCOONH4. The reaction mixture was refluxed for 1 h, filtered through celite pad and evaporated to give a residue. The residue was then dissolved in ethyl acetate, the resulting solution was washed with saturated NaHCO3 aqueous solution, brine, dried over Na2SO4, evaporated to give the final crude product (426 mg, 2.4 mmol, yield: 50%): MS (m/e): 176 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. filtrationfiltered through celite pad
  3. customevaporated
  4. customto give a residue
  5. washthe resulting solution was washed with saturated NaHCO3 aqueous solution, brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-3fbf05d1b7dd46b1afca838e40e4c46d
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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