Water → HCID 45264916, compound

Participants

Reaction Steps

(R)-1-[2-[[2,2-bis(4-Fluoro-2-methylphenyl)ethenyl]oxy]ethyl]-3-piperidine carboxylic acid ethyl ester (1.72 g, 0.0039 mol) (prepared as described in Method D) was dissolved in ethanol (20 ml) and 10N sodium hydroxide solution (4 ml) was introduced. The solution was stirred at room temperature for 3 h and water (100 ml) was added. The solution was extracted with diethyl ether (2×100 ml) and the aqueous phase was acidified to pH 5 with 2N hydrochloric acid solution. Extraction with dichloromethane (4×80 ml) and drying of the combined extracts (MgSO4) followed by evaporation gave a residue, which was dissolved in toluene (50 ml). Methanol (0.16 ml) and chlorotrimethylsilane (0.51 ml) were added, and the product precipitated. The mixture was evaporated to a solid and recrystallized from toluene to give the title compound as a white crystalline solid (0.78 g, 44%), m.p. 175°-185° (decomp.)

Provenance & Evidence