Reaktion #42722

Reaktionsgleichung

water

product

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

product

Hydroxydithien-2-ylacetic Acid Methyl Ester

Sodium hydride

→

title compound

Ausbeute 42.0%

Hydroxydithien-2-ylacetic Acid 9-Methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl Ester

Ausbeute 42.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to ambient temperature
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with water (2×20 mL)
4. 4
   Trocknendried (magnesium sulfate)
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solvent was removed under reduced pressure
7. 7
   SonstigeThe resulting residue was purified by flash chromatography (5% MeOH/DCM)

Vorschrift

The product of step (b) (2.00 g, 12.9 mmol) and the product of step (a) (3.61 g, 14.2 mmol) were melted together at 70° C., under a vacuum of 210 Torr for 1 h. Sodium hydride (60% suspension in oil, 620 mg, 15.5 mmol) was added and the reaction mixture was stirred at 70° C. under 210 Torr for 3 h. The reaction mixture was allowed to cool to ambient temperature and then water (30 mL) and dichloromethane (30 mL) were added. The organic layer was separated and washed with water (2×20 mL), dried (magnesium sulfate), filtered and the solvent was removed under reduced pressure. The resulting residue was purified by flash chromatography (5% MeOH/DCM) to give the title compound as a solid (2.03 g, 5.4 mmol, 42%).

Quelle