Water → HCID 21196303, compound

HRID 1067001Notes

Reaction equation

HRID 1067001 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[C:13]([N:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1)([O:15][CH2:16][CH3:17])=[O:14].O>C1COCC1>[C:13]([N:18]1[CH2:19][CH2:20][C:21]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)([OH:24])[CH2:22][CH2:23]1)([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 122863-BromopyridineHCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 178418339Butyllithium

Product 1

HCID 21196303HCID 21196303, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a flask of THF (200 mL) at −78° C. was added n-butyllithium (24.0 mL, 2.5 M), and the resulting mixture was stirred for 10 min. 3-bromopyridine (5.40 mL, 56.0 mmol) was added to this solution and the resulting mixture was stirred for 30 min. A solution of 1-carbethoxy-4-piperidone (7.24 mL, 48.0 mmol) in THF (20 mL) was cannula to the above anion slowly. The reaction mixture was stirred for 2 hours while warmed to room temperature gradually. Water (100 mL) was added and the mixture was concentrated. Extracted with EtOAc (3×100 mL), the organic extract was dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel with EtOAc and 5% MeOH in EtOAc to give 7.26 g of 1-carbethoxy-4-(3-pyridyl)-4-hydroxyl-piperidine.

Workup

  1. stirringthe resulting mixture was stirred for 30 min
  2. stirringThe reaction mixture was stirred for 2 hours
  3. concentrationthe mixture was concentrated
  4. extractionExtracted with EtOAc (3×100 mL)
  5. extractionthe organic extract
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by column chromatography on silica gel with EtOAc and 5% MeOH in EtOAc

Sources & evidence

ORD record
ord-c7775c8adaff4c95a8d26b72c5406ec1
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

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