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. 2023 Apr 26;66(9):6391–6402. doi: 10.1021/acs.jmedchem.3c00415

Scheme 6. Synthesis of Phenylbicyclo[2.2.2]octaneamine Building Block 8a.

Scheme 6

Reagents and conditions: (a) DIC, 2-hydroxyisoindoline-1,3-dione, 4-DMAP, CH2Cl2, rt, overnight, 55%; (b) (3-methoxyphenyl)magnesium bromide, LiCl, ZnCl2, THF, rt, 1 h; then 6,6′-dimethyl-2,2′-bipyridine, Ni(acac)2, CH3CN, 80 °C, overnight, 83%; (c) BBr3, CH2Cl2, rt, 4 h, 89%; (d) CD3I, K2CO3, CH3CN, 60 °C, 12 h, 94%; (e) LiOH, H2O, MeOH, rt, 12 h, 99%; (f) (Boc)2O, diphenylphosphoryl azide, NEt3, toluene, 80 °C, 12 h, 27%; (g) HCl, MeOH, rt, 3 h, 100%.