Ethanethiol → 1-[2-[2-Hydroxy-4-[6-hydroxy-3-[3-methyl-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine Dioxalate

Participants

Reaction Steps

A solution of 1-[[4-[6-hydroxy-2-[3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy)phenyl]benzo[b]thiophen-3-yl]methyl-2-methylphenyl]methyl]pyrrolidine (Example 127, Part D; 182 mg, 0.327 mmol) in 5 mL of 1,2-dichloroethane was cooled to 0° C. and treated with EtSH (195 μL, 2.62 mmol) followed by AlCl3 (262 mg, 1.96 mmol). The resulting mixture was allowed to warm to ambient temperature. After 16 h, the reaction mixture was poured into 10 mL of saturated aqueous NaHCO3 solution. The aqueous layer was extracted with 5% MeOH/CHCl3 (3×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by radial chromatography (SiO2; gradient of 1% to 4% MeOH in CHCl3, saturated with NH4OH) gave 96 mg (0.177 mmol; 54%) of a white foam. Subsequent dioxalate salt formation as described in Example 1, Part C afforded the title compound as a white solid.

Provenance & Evidence