Dimethylformamide → HCID 69431388, compound

Participants

Reaction Steps

3-Benzyl-8-(3-bromo-phenyl)-3-aza-bicyclo[3.2.1]octan-8-ol (2.17 g, 5.83 mmol) and zinc cyanide (1.03 g, 8.75 mmol) were combined in DMF (30 mL), degassed (evac/N2 purge 3×) then charged with tetrakistriphenylphosphine palladium (0) (3.37 g, 2.91 mmol). The resulting reaction mixture was heated to 85 □ C. in an oil bath for 5 h (or until complete by TLC). After cooling to room temperature, the reaction mixture was filtered through a Celite pad and rinsed with EtOAc. The filtrate was extracted with 1 N HCl (2×50 mL) then neutralized to pH 8 with 1 N NaOH and saturated aqueous NaHCO3 solution, causing an emulsion to form. The product was extracted with EtOAc (3×100 mL), washed with saturated aqueous NaCl solution (2×100 mL), dried over Na2SO4, filtered and concentrated. The resulting crude product was dissolved in ether (100 mL), washed with 50% saturated aqueous NaCl solution (4×100 mL), dried over Na2SO4, filtered and concentrated to a brown oil (1.86 g, 100%). (TLC 40% EtOAc/Hexanes Rf 0.42); 1H NMR (400 MHz, CDCl3) δ 7.76–7.72 (m, 2H), 7.55 (br d, J=7.9 Hz, 1H), 7.45 (t, J=7.9 Hz, 1H), 7.36–7.20 (m, 5H), 3.59 (br s, 2H), 2.84 (d, J=10.8 Hz, 2H), 2.61 (br d, J=10.8 Hz, 2H), 2.36 (br, s, 2H), 1.83 (d, J=7.5 Hz, 2H), 1.35 (m, 2H); APCI MS m/z 319.2 (M+1)+.

Provenance & Evidence