Ammonia → (1R,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine

A solution of 9-methyl-9-azabicyclo[3.3.1]nonan-3-one oxime (10 g, 0.06 moles) in methanol (70 ml) and 0.88 ammonia; (36 ml; 10.0 equivs) was hydrogenated at 50° C. and 50 psi (344.8 kPa)/H2 for 16 hrs using 5% Rhodium on carbon paste (1 g dry weight). The reaction mixture was cooled to room temperature and filtered to remove catalyst. The catalyst bed was washed with methanol and the methanolic solution was then evaporated under reduced pressure to give the title compound as an oil (8.6 g, 93% weight recovery) which solidified to a waxy solid on standing (8.6 g, 93%).

1. customwas hydrogenated at 50° C.
2. dry with material5% Rhodium on carbon paste (1 g dry weight)
3. filtrationfiltered
4. customto remove catalyst
5. washThe catalyst bed was washed with methanol
6. customthe methanolic solution was then evaporated under reduced pressure

ORD record

ord-cc0d3a87311340899db2f5ecccf0561d

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05856489