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

HRID 1095684Notes

Reaction equation

HRID 1095684 reaction equation
C[Si](C)(C)[O:3][C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH:5]=1.[B-](F)(F)(F)[F:20].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[F:20][CH:9]1[C:4](=[O:3])[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8]1

Participants

4

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-CARBOXYLATEYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 4-(trimethylsilyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (64.4 g, 237 mmol) in anhydrous ACN (1.5 L) at ambient temperature was added Selectfluor (92.5 g, 261 mmol) portion wise over 10 minutes, during which a slight exotherm (to 40° C.) was observed. The mixture was stirred for 2 hours, then concentrated to dryness and partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc and the combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to afford 51 g (99%) of desired product as a solid.

Workup

  1. customa slight exotherm (to 40° C.)
  2. concentrationconcentrated to dryness
  3. custompartitioned between EtOAc and brine
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8c77f2edab0344b4b631609d244c5d41
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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