Hydrochloric Acid → 9-Methyl-3-oxa-9-azatricyclo(3.3.1.02,4)nonan-7-ol

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%).

1. stirringstirred for another 24 h at ambient temperature
2. filtrationThe reaction mixture was filtered
3. washthe resulting solid was washed with diethyl ether
4. dissolutionThe dried solid was dissolved in the minimum amount of 10% aqueous potassium carbonate solution
5. extractionextracted with trichloromethane (6×150 mL)
6. dry with materialThe combined organic extracts were dried (magnesium sulfate)
7. filtrationfiltered
8. customthe solvent was removed under reduced pressure

ORD record

ord-39214d042e754036b9a6f6c7890a5e32

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07732441B2