Water → HCID 67402461, compound

HRID 1186433Notes

Reaction equation

HRID 1186433 reaction equation
[F:1][C:2]1([CH:12]([O:17][Si](CC)(CC)CC)[C:13]([F:16])([F:15])[F:14])[CH2:7][CH2:6][N:5]([S:8]([CH3:11])(=[O:10])=[O:9])[CH2:4][CH2:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>O1CCCC1>[F:1][C:2]1([CH:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[CH2:7][CH2:6][N:5]([S:8]([CH3:11])(=[O:10])=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 67402255HCID 67402255, compound

Product 1

HCID 67402461HCID 67402461, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

By use of 4-fluoro-1-methanesulfonyl-4-[2,2,2-trifluoro-1-(triethyl-siloxy)ethyl]piperidine (309 mg, 0.785 mmol) dissolved in tetrahydrofuran (5 mL) and a 1 mol/L solution of tetrabutylammonium fluoride in tetrahydrofuran (1.18 mL, 1.18 mmol), the mixture was stirred and reacted at room temperature for 30 minutes. The reaction was stopped by addition of water to the reaction mixture, and extraction with ethyl acetate was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give Compound EAS (120 mg, yield: 55%).

Workup

  1. customreacted at room temperature for 30 minutes
  2. dry with materialby drying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)
  5. customto give Compound EAS (120 mg, yield: 55%)

Sources & evidence

ORD record
ord-73d9b40b8702478d9432f6fec116fcf2
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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