(S)-(+)-4-(oxiranylmethoxy)-2,3-dihydrobenzo[b]furan → (2s)-(-)-1-(2,3-Dihydro-4-benzo[b]furanoxy)-3-(4-(3-methylbenzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol oxalate

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Reaction Steps

A solution 4-hydroxy-4-(3-methylbenzo[b]thiophen-2-yl)piperidine (0.070 g, 0.303 mmol, prepared in example 11) and (S)-(+)-4-(oxiranylmethoxy)-2,3-dihydrobenzo[b]furan (0.058 g, 0.303 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) to give the free base of the title compound as a clear colorless oil (0.067 g, 52%). The oxalate salt was prepared to give the title compound. FDMS, m/e=424 (M++1 of free base). [α]D=−9.09 (c=0.44, methanol). C25H29NO3S.C2H2O4

Provenance & Evidence