4-Hydroxy-4-(3-methylbenzo[b]thiophen-2-yl)piperidine → (2S)-(-)-1-(4-Benzo[b]furanoxy)-3-(4-(3-methylbenzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol Hemihydrate

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A solution 4-hydroxy-4-(3-methylbenzo[b]thiophen-2-yl)piperidine (0.074 g, 0.320 mmol) and (S)-(+)-4-(oxiranylmethoxy)-benzo[b]furan (0.061 g, 0.320 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/1% methanol in dichloromethane gradient elution) to give the final title compound as a clear colorless oil (0.057 g, 42%). FDMS m/e=422 (M++1). C25H27NO3S.0.5H2O

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