Selectfluor → TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATE

HRID 451554Notes

Reaction equation

HRID 451554 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([O:14][Si](C)(C)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:19][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>C(#N)C.[Cl-].[Na+].O>[F:19][CH:10]1[C:11](=[O:14])[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 10778540tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 10560711TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATE

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-Trimethylsilyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (13.2 g, 48.6 mmol) was dissolved in acetonitrile (250 mL). 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (19.0 g, 53.5 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours. Brine was added to the reaction mixture and the aqueous phase extracted ethyl acetate. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, 100 g, 0% to 100% EtOAc in heptane). The title compound was obtained as white solid (5.66 g, 53%).

Workup

  1. extractionthe aqueous phase extracted ethyl acetate
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash chromatography (silica gel, 100 g, 0% to 100% EtOAc in heptane)

Sources & evidence

ORD record
ord-271598a35ef146bc8a5ac51e69932705
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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