Hydrochloric Acid → 4-Methoxy-9-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene

Temperature

-10 °C

1 M Borane tetrahydrofuran complex (70 mL) is added dropwise to a solution of 4-methoxy-9-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-trien-10-one (3.0 g) in tetrahydrofuran (20 mL) chilled in an ice bath. The resulting solution is stirred at reflux temperature for 5 h and then at room temperature overnight. The solution is cooled to ca. −10° C. and half-concentrated hydrochloric acid (50 mL) is added carefully. The mixture is stirred at room temperature for 1 h and an additional hour at reflux temperature. The solvent is removed and 2 M aqueous NaOH solution (50 mL) is added to the residue. The resulting mixture is extracted with dichloromethane and the combined organic extracts are dried (MgSO4). After removal of the solvent, the residue is taken up in ethanol (20 mL) and the resulting solution is treated with oxalic acid (3 mL) to obtain the oxalate salt of the title compound.

1. temperaturechilled in an ice bath
2. temperatureat reflux temperature for 5 h
3. customat room temperature
4. customovernight
5. stirringThe mixture is stirred at room temperature for 1 h and an additional hour
6. temperatureat reflux temperature
7. customThe solvent is removed
8. addition2 M aqueous NaOH solution (50 mL) is added to the residue
9. extractionThe resulting mixture is extracted with dichloromethane
10. dry with materialthe combined organic extracts are dried (MgSO4)
11. customAfter removal of the solvent
12. additionthe resulting solution is treated with oxalic acid (3 mL)

ORD record

ord-0a6ac8828b6e4d6cbfa9dce881af23ca

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765780B2