Thionyl Chloride → Methyl 1-azabicyclo[2.2.2]oct-2-ene-3-carboxylate--hydrogen chloride (1/1)

HRID 1650878Notes

Reaction equation

HRID 1650878 reaction equation
S(Cl)([Cl:3])=O.O[C:6]1([C:14]([O:16][CH3:17])=[O:15])[CH:11]2[CH2:12][CH2:13][N:8]([CH2:9][CH2:10]2)[CH2:7]1>>[ClH:3].[N:8]12[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9]1)[C:6]([C:14]([O:16][CH3:17])=[O:15])=[CH:7]2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2824485Methyl 3-hydroxy-1-azabicyclo[2.2.2]octane-3-carboxylate

Product 1

HCID 23053204Methyl 1-azabicyclo[2.2.2]oct-2-ene-3-carboxylate--hydrogen chloride (1/1)Yield 75.3%

Procedure

1,180 g of thionyl chloride were sufficiently cooled so that upon portionwise addition of 150 g (0.81 mole) of methyl 3-hydroxy-quinuclidine-3-carboxylate of Example 2, a temperature of 15° C. was not exceeded. Then, the mixture was refluxed for 15 hours and subsequently excess thionyl chloride was distilled off. The residue was admixed at elevated temperature with 350 ml of isopropanol, again heating at reflux. After cooling to room temperature, the suspension was filtered and the residue was washed with 80 ml of isopropanol and dried to obtain 123 g (0.61 mole) of methyl 1-azabicyclo(2,2,2)oct-2-ene-3-carboxylate hydrochloride (75% yield) having a melting point of 175° to 177° C.

Workup

  1. customa temperature of 15° C.
  2. temperatureThen, the mixture was refluxed for 15 hours
  3. distillationsubsequently excess thionyl chloride was distilled off
  4. temperatureagain heating
  5. temperatureat reflux
  6. filtrationthe suspension was filtered
  7. washthe residue was washed with 80 ml of isopropanol
  8. customdried

Sources & evidence

ORD record
ord-aec58e11be9d49a79eab34672f1175bf
Source dataset
uspto-grants-1990_05
Patent number
US04925942

Reaction notes

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