4-(6-Fluoronaphth-2-yl)piperidine → (2S)-(+)-1-(2,3-Dihydrobenzo[b]furan-4-yl)oxy-3-(4-(6-fluoronaphth-2-yl)piperidin-1-yl)-2-propanol

Participants

Reaction Steps

A solution 4-(6-fluoronaphth-2-yl)piperidine (0.075 g, 0.327 mmol) and (S)-(+)-4-(oxiranylmethoxy)-2,3-dihydrobenzo[b]furan (0.063 g, 0.327 mmol) in methanol (3 mL) was heated at reflux for 18 hours and then cooled and evaporated. The residue was purified using silica gel chromatography (dichloromethane/5% methanol in dichloromethane gradient elution) to give the title compound as a white amorphous solid (0.036 g, 26%). FDMS m/e=422 (M++1). [α]D=21.65 (c 0.508, methanol). C26H28FNO3.

Provenance & Evidence