8-[3-Bromo-4-(2-chloro-4-nitrophenoxy)-2,5-dimethylphenyl]-8-azabicyclo[4.3.0]-nonan-7,9-dione → 8-[4-(4-Amino-2-chlorophenoxy)-3-bromo-2,5-dimethylphenyl]-8-azabicyclo[4.3.0]-nonan-7,9-dione

Participants

Reaction Steps

Into a Parr bottle was charged 8-[3-bromo-4-(2-chloro-4-nitrophenoxy)-2,5-dimethylphenyl]-8-azabicyclo[4.3.0]-nonan-7,9-dione (3.45 grams, 6.79 mmol) prepared in Part D and ethyl acetate (100 milliliters). The reaction mixture was purged with nitrogen, 5% platinum on carbon (480 milligrams) was added and the mixture was hydrogenated for 1.5 hours at 40-50 psi hydrogen and room temperature on a rocking Parr hydrogenator. Filtration through celite and concentration under reduced pressure afforded the desired product (2.73 grams, 5.71 mmol, 84%). H'-NMR (CDCl3) 6.93 (br s, 1H), 6.80 (d, J=2 Hz, 1H), 6.33 (m, 2H), 3.45 (br s, 2H), 3.06 (br m, 2H) 2.4-1.2 (m, 14H).

Provenance & Evidence