Ethyl 4-oxo-1-piperidinecarboxylate → HCID 69264426, compound

HRID 899261Notes

Reaction equation

HRID 899261 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:28])[CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([Li])CCC.[O:34]=[C:35]1[CH2:40][CH2:39][N:38]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:37][CH2:36]1>O1CCCC1>[Si:11]([O:10][CH2:9][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:35]1([OH:34])[CH2:36][CH2:37][N:38]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:39][CH2:40]1)[OH:28])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 69264442HCID 69264442, compoundHCID 178418339Butyllithium

Product 1

HCID 69264426HCID 69264426, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of 1-(2-bromophenyl)-2-{[tert-butyl(diphenyl)silyl]oxy}ethanol (step 2, 5.63 g, 12.4 mmol) in tetrahydrofuran (36 mL) was added dropwise a 1.59 M solution of butyllithium in tetrahydrofuran (15.9 mL, 25.3 mmol) at −78° C. for 5 min and the mixture was stirred for 5 h at the same temperature. To the mixture was added dropwise a solution of ethyl 4-oxopiperidine-1-carboxylate (2.33 g, 13.6 mmol) in tetrahydrofuran (10 mL) at −78° C. and the mixture was stirred for 2 h at the same temperature. This resulting mixture was slowly warmed up to room temperature and stirred for 16 h at the same temperature. The reaction mixture was quenched by the addition of saturated ammonium chloride aqueous solution, and concentrated to give a yellow residue. The crude material was partitioned between ethyl acetate and water, and then the organic layer washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (150 g) eluting with hexane/ethyl acetate (2/1) to afford 1.76 g (26%) of the title compound as a colorless solid:

Workup

  1. stirringthe mixture was stirred for 2 h at the same temperature
  2. stirringstirred for 16 h at the same temperature
  3. customThe reaction mixture was quenched by the addition of saturated ammonium chloride aqueous solution
  4. concentrationconcentrated
  5. customto give a yellow residue
  6. customThe crude material was partitioned between ethyl acetate and water
  7. washthe organic layer washed with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customThe residue was purified by column chromatography on silica gel (150 g)
  11. washeluting with hexane/ethyl acetate (2/1)

Sources & evidence

ORD record
ord-b03f80068f6d4c9a8b20058e8c4afe92
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

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