Ethyl 4-oxo-1-piperidinecarboxylate → HCID 13839462, compound

HRID 1616207Notes

Reaction equation

HRID 1616207 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:13]([Li])[CH2:14][CH2:15][CH3:16]>O1CCCC1.[Cl-].[NH4+]>[CH2:13]([C:2]1([OH:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1)[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 178418339Butyllithium

Product 1

HCID 13839462HCID 13839462, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

Under an atmosphere of argon, to a solution of ethyl 4-oxo-1-piperidinecarboxylate (1.00 g) in anhydrous tetrahydrofuran (5 mL) was added n-butyl lithium (1.56M hexane solution, 5.62 mL) at −40° C. The reaction mixture was stirred at 0° C. for 2 hours. The reaction mixture was poured in saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The organic layer was washed with a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified with column chromatography on silica gel (hexane:ethyl acetate=7:3) to give the title compound (269 mg) having the following physical data.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified with column chromatography on silica gel (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-892bb347cdf644ce842db4e4f1c7f47f
Source dataset
uspto-grants-2014_07
Patent number
US08765783B2

Reaction notes

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