Ammonium formate → HCID 53641593, compound

HRID 1809949Notes

Reaction equation

HRID 1809949 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-befb1b22d4114cbf83a9c4dc78d55f26
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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