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

HRID 1468001Notes

Reaction equation

HRID 1468001 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.C(OCC)(=O)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

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-CARBOXYLATEYield 78%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of tert-butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate (2.15 g, 7.92 mmol) in anhydrous acetonitrile (20 mL), selectfluor (3.08 g, 8.71 mmol) was added and stirred at room temperature for 1-2 h. The reaction mixture was diluted with ethyl acetate and washed with saturated NaHCO3 solution. The organic layer was separated, concentrated in vacuo and the residue was purified by flash column chromatography to yield tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate as a white solid (1.34 g, 78%). 1H NMR (400 MHz, CDCl3) δ; 1.50 (s, 9H), 2.49-2.63 (m, 2H), 3.20-3.27 (m, 2H), 4.11-4.21 (m, 2H), 4.76-4.80 (m, 0.5H), 4.88-4.92 (m, 0.5H).

Workup

  1. washwashed with saturated NaHCO3 solution
  2. customThe organic layer was separated
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-13d83d0aba7a44819fa9dda06e18c587
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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