Ethyl Acetate → HCID 57541275, compound

HRID 1677048Notes

Reaction equation

HRID 1677048 reaction equation
CC(C)([O-:4])C.[K+].ON=[C:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.F[C:23]1[CH:28]=[CH:27]C=C[N:24]=1.CCO[C:32]([CH3:34])=[O:33]>CN(C=O)C.CCCC(C)C>[O:4]=[C:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]1[C:34]1[C:32](=[O:33])[NH:24][CH:23]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 97462-FluoropyridineHCID 15462924tert-Butyl 4-(hydroxyimino)piperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 57541275HCID 57541275, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 78922-MethylpentaneSolvent

Procedure

Potassium tert-butoxide (1.22 g, 10.8 mmol) were added to tert-butyl 4-(hydroxyimino)piperidine-1-carboxylate (2.11 g, 9.85 mmol) in DMF (10 mL) at 0° C. under argon. The resulting suspension was stirred for 20 mins. 2-Fluoropyridine (0.85 mL, 9.85 mmol) was added to the reaction mixture and the resulting solution was stirred at 80° C. for 21 hours. The reaction mixture was poured into ice water (100 mL) and extracted with EtOAc (2×50 mL). The organic layers were combined and washed with brine (2×50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. Flash column chromatography (silica, gradient 5 to 100% EtOAc in isohexane) yielded tert-butyl 4-oxo-3-(2-oxo-1,2-dihydropyridin-3-yl)piperidine-1-carboxylate (0.654 g, 23%) as a cream solid.

Workup

  1. stirringthe resulting solution was stirred at 80° C. for 21 hours
  2. extractionextracted with EtOAc (2×50 mL)
  3. washwashed with brine (2×50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto afford crude product

Sources & evidence

ORD record
ord-932aa6186c994b4ea2dcc14fe3174fdc
Source dataset
uspto-grants-2011_08
Patent number
US08008279B2

Reaction notes

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