Sodium Cyanide → HCID 90408367, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(3-fluoro-5-(tetrahydro-2H-pyran-2-yloxy)phenyl)-4-(iodomethyl)-2-oxabicyclo[2.2.2]octane (732 mg, 1.640 mmol), 18-crown-6 (43 mg, 0.164 mmol), and NaCN (88 mg, 1.80 mmol) in DMF (1 mL) was stirred at 40° C. under N2 for 18 h. The reaction was cooled to rt and filtered. The filtrate was concentrated in vacuo. The residue was taken up in DCM (50 mL) and filtered. The residual solid was washed with DCM (10 mL×2). The combined organic filtrates were concentrated in vacuo. The crude oil was purified by flash chromatography (SiO2) using a 0% to 30% EtOAc/hexane gradient (15 min) to give the title compound (560 mg, 1.62 mmol, 99% yield) as a white solid.

Provenance & Evidence