1-(2-Cyclopentyl-2-oxo-ethyl)-2-methyl-pyridinium bromide salt → 2-Cyclopentyl-indolizine

HRID 37825Notes

Reaction equation

HRID 37825 reaction equation
[Br-].[CH:2]1([C:7](=O)[CH2:8][N+:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[CH2:6][CH2:5][CH2:4][CH2:3]1>C(=O)(O)[O-].[Na+].O>[CH:2]1([C:7]2[CH:15]=[C:10]3[N:9]([CH:8]=2)[CH:14]=[CH:13][CH:12]=[CH:11]3)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 866395921-(2-Cyclopentyl-2-oxo-ethyl)-2-methyl-pyridinium bromide salt

Product 1

HCID 668510452-Cyclopentyl-indolizineYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-(2-Cyclopentyl-2-oxo-ethyl)-2-methyl-pyridinium bromide salt (3.4 g, 12.0 mmol) was heated at reflux in saturated sodium bicarbonate solution for 3 hrs. The mixture was allowed to cool, diluted with water and extracted with ethyl acetate (×2). The combined organic phases were washed with water and brine, dried over sodium sulfate and concentrated to give a residue which was purified by column chromatography using 100-200 mesh silica-gel and 1% ethyl acetate/petroleum-ether as eluent to afford 2-cyclopentyl-indolizine (0.91 g, 41%) as a solid.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9a3e7006b0a64d7283a6e76b01cb7168
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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