Ammonium formate → HCID 53641593, compound

HRID 338975Notes

Reaction equation

HRID 338975 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+]>C(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

5

Reactant 2

HCID 2723923Ammonium formateHCID 54443836HCID 54443836, compound

Product 1

HCID 53641593HCID 53641593, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 1-benzyl-3-(fluoromethyl)pyrrolidine-3-carboxylate (2.98 g, 11.2 mmol) and ammonium formate (3.54 g, 56.2 mmol) in ethanol (100 mL) was flushed with nitrogen for 15 minutes. 10% Pd/C (1.2 g, 1.12 mmol) was added and the mixture heated at reflux for 30 minutes. The reaction mixture was cooled to ambient temperature, filtered through a pad of Celite, washing with ethanol (50 mL). The filtrate was concentrated under reduced pressure to afford ethyl 3-(fluoromethyl)pyrrolidine-3-carboxylate (1.86 g, 95%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 30 minutes
  3. filtrationfiltered through a pad of Celite
  4. washwashing with ethanol (50 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-827c0b8412934eb7bfa12f9989a958bc
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

Loading…