Acetic Acid → 4-{[(2S)-2-fluoropropyl]oxy}piperidine

HRID 69126Notes

Reaction equation

HRID 69126 reaction equation
[F:1][C@@H:2]([CH3:11])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.C(O)(=O)C>CO.[Pd]>[F:1][C@@H:2]([CH3:11])[CH2:3][O:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 666961134-{[(2S)-2-fluoropropyl]oxy}pyridine

Product 1

HCID 866943284-{[(2S)-2-fluoropropyl]oxy}piperidineYield 43.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.2 g of 4-{[(2S)-2-fluoropropyl]oxy}pyridine was added to a solution of 22 mL of acetic acid in 22 mL of methanol, and 500 mg of 10% palladium on carbon (wet type) was added thereto under an argon atmosphere. The mixture was stirred at room temperature overnight under a hydrogen atmosphere of 3 atm. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (chloroform/methanol) to obtain 988 mg of 4-{[(2S)-2-fluoropropyl]oxy}piperidine.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-5bcb731dbce54b409b27b111188b01a7
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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