Sodium Bicarbonate → 1-Allyloxycarbonyl-3-acetyl-1,2,5,6-tetrahydropyridine

HRID 1029620Notes

Reaction equation

HRID 1029620 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]=[C:9]([C:13]2([CH3:18])OCC[O:14]2)[CH2:8]1)=[O:6])[CH:2]=[CH2:3].O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CC(C)=O>[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]=[C:9]([C:13](=[O:14])[CH3:18])[CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 151172242-(1-Allyloxycarbonyl-1,2,5,6-tetrahydropyridin-3-yl)-2-methyl-1,3-dioxolaneHCID 86626551p-Toluenesulfonic acid dihydrate

Product 1

HCID 151172251-Allyloxycarbonyl-3-acetyl-1,2,5,6-tetrahydropyridineYield 77.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(1-allyloxycarbonyl-1,2,5,6-tetrahydropyridin-3-yl)-2-methyl-1,3-dioxolane (6.95 g) in acetone (140 ml) was added p-toluenesulfonic acid dihydrate (523 mg) at room temperature and the mixture was stirred at the same temperature for 1 hour. Then, saturated aqueous sodium hydrogen carbonate solution was added for neutralization of the acid and the reaction mixture was concentrated under reduced pressure. The concentrate was diluted with ethyl acetate and water, followed by stirring, and the aqueous layer was separated and extracted with 2 portions of ethyl acetate. The organic layers were combined, washed successively with saturated aqueous sodium hydrogen carbonate solution, water and aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by column chromatography to give 1-allyloxycarbonyl-3-acetyl-1,2,5,6-tetrahydropyridine (4.43 g).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe concentrate was diluted with ethyl acetate and water
  3. stirringby stirring
  4. customthe aqueous layer was separated
  5. extractionextracted with 2 portions of ethyl acetate
  6. washwashed successively with saturated aqueous sodium hydrogen carbonate solution, water and aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was then distilled off under reduced pressure
  9. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-eda07455254a4f1ba9e36d9be352ced6
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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