Hydrochloric Acid → 3-Ethenyl-3-hydroxy-1-azabicyclo[2.2.2]octane

HRID 841061

Reaktionsgleichung

Reaktionsgleichung von HRID 841061
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[CH2:2]2.[CH:10]([Mg]Br)=[CH2:11].Cl.[OH-].[Na+]>O1CCCC1>[CH:10]([C:3]1([OH:9])[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)=[CH2:11]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 195073-QuinuclidinoneHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 226207783-Ethenyl-3-hydroxy-1-azabicyclo[2.2.2]octaneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Under an argon atmosphere, a solution of 3-quinuclidinone (1.25 g, 10 mmol) in anhydrous tetrahydrofuran (10 mL) was added over 15 minutes to a 1 M solution of vinylmagnesium bromide in tetrahydrofuran (20 mL, 20 mmol) at 0° C. to 5° C., stirred at room temperature for 24 hours, cooled to 0° C., and acidified to pH 1 with 6 M hydrochloric acid. The mixture was stirred for 15 minutes, basified to pH 10 with 25% aqueous sodium hydroxide, extracted with chloroform (4×50 mL) and chloroform/methanol (4:1, 50 mL), combined the organic layers, dried (MgSO4), evaporated under reduced pressure and purified by flash chromatography (eluting with ammoniated chloroform/methanol, 85:15) to obtain the title compound (830 mg, 5.4 mmol, 54%).

Aufarbeitung

  1. temperaturecooled to 0° C.
  2. stirringThe mixture was stirred for 15 minutes
  3. extractionextracted with chloroform (4×50 mL) and chloroform/methanol (4:1, 50 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. custompurified by flash chromatography (eluting with ammoniated chloroform/methanol, 85:15)

Quellen und Nachweise

ORD-Eintrag
ord-0ad556cb2f2248b3bacf7437056b04dc
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06369224B1

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