4-(6-Fluoronaphth-2-yl)piperidine → (2S)-(+)-1-(4-Benzo[b]furanoxy)-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)benzo[b]furan (0.062 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 final title compound as a white amorphous solid (0.050 g, 37%). FDMS m/e=420 (M++1). [α]D=11.31 (c 0.531, methanol). C26H26FNO3.

Provenance & Evidence