(3aR,5R,6aR)-Benzyl 5-((3-methoxytetrahydro-2H-pyran-4-yl)amino)-3a-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)hexahydrocyclopenta-[c]pyrrole-2(1H)-carboxylate → ((3aR,5R,6aR)-5-(((3S*,4S*)-3-Methoxytetrahydro-2H-pyran-4-yl)amino)octahydro-cyclopenta[c]pyrrol-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

Participants

Reaction Steps

A solution of the product from Step B (1.53 g, 2.55 mmol) in methanol (18 mL) was bubbled with Ar for 15 min, and 10% Palladium on carbon (0.3 g) was added. The mixture was hydrogenated at 25 psi in Parr shaker overnight. Filtration and evaporation to dryness gave the product as yellow foam. 1H-NMR (400 MHz, CDCl3): δ 1.37-2.04 (m, 7H), 2.21 (d, J=5.8 Hz, 1H), 2.47-2.63 (m, 1H), 2.66-2.86 (m, 1H), 2.86-3.54 (m, 12H), 3.60 (br. s., 1H), 3.66-4.21 (m, 4H), 4.61-5.05 (m, 2H), 7.70 (br. s., 1H), 8.71 (br. s., 1H); LC/MS: C23H31F3N4O3: m/z 469.2 (M+H).

Provenance & Evidence