Reaction #42722

Reaction equation

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

Yield 42.0%

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

Yield 42.0%

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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%).

Source