Reaktion #42721

Reaktionsgleichung

Sodium borohydride

scopolamine

hydrochloric acid

→

title compound

Ausbeute 50.0%

9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol

Ausbeute 50.0%

Lösungsmittel

ethanol

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for another 24 h at ambient temperature
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Waschenthe resulting solid was washed with diethyl ether
4. 4
   workup.DISSOLUTIONThe dried solid was dissolved in the minimum amount of 10% aqueous potassium carbonate solution
5. 5
   Extraktionextracted with trichloromethane (6×150 mL)
6. 6
   TrocknenThe combined organic extracts were dried (magnesium sulfate)
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe solvent was removed under reduced pressure

Vorschrift

Sodium borohydride (39.0 g, 1.03 mol) was added portionwise to a stirred suspension of scopolamine (75 g, 171 mmol) in ethanol (743 mL), at 0° C. under a nitrogen atmosphere and the reaction mixture was stirred at ambient temperature for 24 h. The mixture was then acidified with 2M hydrochloric acid in diethyl ether (600 mL) and stirred for another 24 h at ambient temperature. The reaction mixture was filtered and the resulting solid was washed with diethyl ether. The dried solid was dissolved in the minimum amount of 10% aqueous potassium carbonate solution and extracted with trichloromethane (6×150 mL). The combined organic extracts were dried (magnesium sulfate), filtered and the solvent was removed under reduced pressure to give the title compound as crystals (13.2 g, 85.5 mmol, 50%).

Quelle