Ammonium formate → HCID 53641593, compound

HRID 1173287Notes

Reaction equation

HRID 1173287 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-14e5eae5543942ac95a243f878412510
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Reaction notes

Loading…