Trifluoroacetic acid → HCID 86757211, compound

Participants

Reaction Conditions

Reaction Steps

A slurry of 45 mg of LiAlH4 in 10 mL of THF was cooled to 0° C. and was treated with a solution of 200 mg (0.37 mmol) of 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 4-[2-(1-pyrrolidinyl)ethoxy]phenyl ketone (Part D) in 5 mL of THF. The reaction was stirred at 0° C. for 2 h and was quenched by the sequential addition of 1 mL of H2O, 1 mL of 2 N aq NaOH, and 1 mL of H2O. The two layers were separated and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers were washed with 25 mL of brine, dried over K2CO3, and evaporated in vacuo. The residue was taken up in 10 mL of CH2Cl2, cooled to 0° C., and treated with 0.47 mL (2.94 mmol) of triethylsilane. After stirring at 0° C. for 6 h, the reaction was treated with 0.3 mL (3.9 mmol) of TFA, followed by an additional 16 h of stirring at 0° C. The reaction mixture was poured into 10 mL saturated aq NaHCO3 and the two layers were separated. The aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organic layers were dried over K2CO3 and evaporated in vacuo to give 233 mg of an oil which was purified by radial chromatography (SiO2; gradient 2-10% MeOH in CH2Cl2) to afford 158 mg (0.30 mmol; 81%) of the title compound as the free base. Conversion to the dioxalate salt was effected by the procedure detailed in Example 1, Part C.

Provenance & Evidence