HCID 22645922, compound → 3,3,4,4-Tetrafluoropyrrolidine Hydrochloride

HRID 2414456Notes

Reaction equation

HRID 2414456 reaction equation
[ClH:1].C([N:9]1[CH2:13][C:12]([F:15])([F:14])[C:11]([F:17])([F:16])[CH2:10]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[ClH:1].[F:16][C:11]1([F:17])[C:12]([F:15])([F:14])[CH2:13][NH:9][CH2:10]1

Participants

5

Reactant 2

HCID 22645922HCID 22645922, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 226459203,3,4,4-Tetrafluoropyrrolidine Hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzyl-3,3,4,4-tetrafluoro-pyrrolidine hydrochloride (23.8 grams, 88 mmol) in ethanol (300 mL) containing 10% palladium on carbon was treated with hydrogen in a Parr shaker at 45 psi for 3 hours. The mixture was filtered through Celite®, the filtrate was concentrated to dryness. The residue was triturated with ether and the solid was collected and dried (13.4 grams, 85%, (melting point: 193-196° C.). 1H NMR (400 MHz, D2O) 3.93 (m, 4H), 7.26-7.41 (m, 5H). 19F NMR (376 MHz, D2O) δ−122.25 (m)

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was triturated with ether
  4. customthe solid was collected
  5. customdried (13.4 grams, 85%, (melting point: 193-196° C.)

Sources & evidence

ORD record
ord-18ced41abe4743eaa9a2cc076544841d
Source dataset
uspto-grants-2004_11
Patent number
US06812350B2

Reaction notes

Loading…