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

HRID 2280377Notes

Reaction equation

HRID 2280377 reaction equation
N#N.C[Si](C)(C)[O:5][C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH:7]=1.[B-](F)(F)(F)[F:22].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.CC(=O)OCC>C(#N)C>[F:22][CH:11]1[C:6](=[O:5])[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 8857Ethyl AcetateHCID 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 1

HCID 6342AcetonitrileSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of tert-butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate (5.00 g, 18.40 mmol) in dry acetonitrile (25 mL) was added Selectfluor® (7.55 g, 20.3 mmol) at rt. The reaction mixture was stirred at rt for 2 h then poured into EA and successively washed with aq. 1% NaHCO3 and brine. The org. layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by FC (hexanes/EA, 4:1) to afford the title compound as a pale yellow solid. LC-MS-conditions 08: tR=0.55 min; [M-CH3+H]+=203.23; TLC: rf (hexanes/EA, 4:1)=0.17.

Workup

  1. washsuccessively washed with aq. 1% NaHCO3 and brine
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by FC (hexanes/EA, 4:1)

Sources & evidence

ORD record
ord-fb3ce4ad9c124b35b754e6b0acbe4916
Source dataset
uspto-grants-2015_09
Patent number
US09139524B2

Reaction notes

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