HCID 67421578, compound → HCID 67420337, compound

Participants

Reaction Steps

To a solution of 3,3″-dimethyl-1′-(2-nitro-benzyl)-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (0.55 g, 1.37 mmol) in MeOH (20 mL) was added palladium (50% wet with water), 10 wt.% on activated carbon (0.113 g). The resultant mixture was hydrogenated at 30 psi on a Parr shaker for 3 hours. The mixture was vacuum filtered through celite and the cake was washed with MeOH. The solvent was removed from the filtrate under reduced pressure and the thus obtained oil was purified by radial chromatography on silica gel (2 mm plate, 100:1:1 CH2Cl2—CH3OH—NH4OH) and provided 80 mg (16%) of COMPOUND 65 as a white solid. 1H NMR (CDCl3) δ 1.49-1.72 (m, 3H), 1.88-1.95 (m, 1H), 2.06-2.20 (m, 2H), 2.36 (s, 6H), 3.33 (s, 2H), 3.75 (dd, 2H, J=11.7, 3.0 Hz), 4.47 (br s, 2H), 6.07 (dd, 2H, J=7.5, 6.0 Hz), 6.42-6.45 (m, 1H), 6.54 (td, 1H, J=7.5, 1.2 Hz), 6.87 (dd, 2H, J=7.5, 4.8 Hz), 7.15 (d, 2H, J=7.5 Hz), 8.33 (d, 2H, J=3.9 Hz); ES-MS m/z 373 (M+H).

Provenance & Evidence