Ammonium formate → tert-Butyl (3-(fluoromethyl)pyrrolidin-3-yl)carbamate

HRID 338978Notes

Reaction equation

HRID 338978 reaction equation
C([CH:8]1[C:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH2:13][F:14])[CH2:11][CH2:10][N:9]1C(OCC)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[F:14][CH2:13][C:12]1([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:11][CH2:10][NH:9][CH2:8]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 70984687Ethyl benzyl-3-(tert-butoxycarbonylamino)-3-(fluoromethyl)pyrrolidine-1-carboxylate

Product 1

HCID 19691539tert-Butyl (3-(fluoromethyl)pyrrolidin-3-yl)carbamateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl benzyl-3-(tert-butoxycarbonylamino)-3-(fluoromethyl)pyrrolidine-1-carboxylate (2.27 g, 6.44 mmol) and ammonium formate (3.03 g, 32.2 mmol) in ethanol (60 mL) was flushed with nitrogen for 15 minutes. 10% Pd/C (0.69 g, 0.644 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 and washed with ethanol (30 mL) and concentrated under reduced pressure to afford tert-butyl 3-(fluoromethyl)pyrrolidin-3-ylcarbamate (1.4 g, 100%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 30 minutes
  3. filtrationfiltered through a pad of Celite
  4. washwashed with ethanol (30 mL)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-32eccf095e224179a96387874a40e7cf
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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