Sodium Cyanide → HCID 90408448, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(1-(3-fluoro-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethyl methanesulfonate (0.45 g, 1.05 mmol), NaCN (0.309 g, 6.30 mmol), and Bu4NI (0.039 g, 0.105 mmol) in DMSO (10 mL) was stirred at 85° C. for 18 h, then was cooled to rt and diluted with EtOAc (10 mL). The organic phase was washed with water (3×), dried (MgSO4), filtered, and concentrated in vacuo. The residual crude oil was chromatographed (SiO2; gradient from 0% to 30% EtOAc/hexane over 10 min) to give the title compound (0.348 g, 0.968 mmol, 92% yield) as a clear oil. 1H NMR (CDCl3) δ: 6.86 (t, J=1.8 Hz, 1H), 6.74 (dt, J=10.1, 1.9 Hz, 1H), 6.69 (dt, J=10.6, 2.3 Hz, 1H), 5.40 (t, J=3.2 Hz, 1H), 3.93-3.86 (m, 1H), 3.85-3.81 (m, 2H), 3.62 (dtd, J=11.4, 4.1, 1.4 Hz, 1H), 2.32 (dd, J=8.6, 7.3 Hz, 2H), 2.07-1.96 (m, 4H), 1.88-1.80 (m, 2H), 1.79-1.55 (m, 10H); 19F NMR (CDCl3) δ: −111.9.

Provenance & Evidence