Sodium Carbonate → tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

HRID 1392753Notes

Reaction equation

HRID 1392753 reaction equation
[C:1](OC([O-])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:12]1[CH2:17][CH:16]=[CH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>O>[N:12]1([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH:14]=[CH:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 127501,2,3,6-TetrahydropyridineHCID 22064466Tert-butyldicarbonate

Product 1

HCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylateYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl dicarbonate (6.55 g) was added to a mixture of 1,2,3,6-tetrahydropyridine (2.50 g) and a 10% aqueous solution (3.0 ml) of sodium carbonate, and the mixture was stirred at room temperature for 20 hours. Water was added to the reaction mixture to conduct extraction with ethyl acetate. The resultant organic layer was washed with 0.5N hydrochloric acid, water, a saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride in that order and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure to obtain the title compound (5.08 g).

Workup

  1. extractionextraction with ethyl acetate
  2. washThe resultant organic layer was washed with 0.5N hydrochloric acid, water
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride in that order and dried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-ee90f3a13543433db3ddfd92551d211e
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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