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-e2a38c19cca54e2db9ee98ee3ed96dc9

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07358244B2