Reacción #42722

Ecuación de reacción

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

Rendimiento 42.0%

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

Rendimiento 42.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool to ambient temperature
2. 2
   OtroThe organic layer was separated
3. 3
   Lavadowashed with water (2×20 mL)
4. 4
   Secadodried (magnesium sulfate)
5. 5
   Filtraciónfiltered
6. 6
   Otrothe solvent was removed under reduced pressure
7. 7
   OtroThe resulting residue was purified by flash chromatography (5% MeOH/DCM)

Procedimiento

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%).

Fuente