Thionyl Chloride → 1-Azabicyclo[2.2.2]oct-2-ene-3-carboxylic acid methyl ester Hydrochloride

HRID 1650878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1650878
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

Komponenten

3

Edukt 2

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

Produkt 1

HCID 230532041-Azabicyclo[2.2.2]oct-2-ene-3-carboxylic acid methyl ester HydrochlorideAusbeute 75,3 %

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-aec58e11be9d49a79eab34672f1175bf
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925942

Notizen zur Reaktion

Wird geladen…