1-[2-[4-[3-[4-[3-(1-Pyrrolidinyl)-1-propynyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine Dioxalate → (E)-1-[2-[4-[3-[4-[3-(1-Pyrrolidinyl)-1-propenyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine Dioxalate

Participants

Reaction Steps

A solution of 1-[2-[4-[3-[4-[3-(1-pyrrolidinyl)-1-propynyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine (Example 129, Part D; 300 mg, 0.576 mmol) in 40 mL of pyridine was treated with a slurry of Lindlar catalyst (Pd/CaCO3, Pb poisoned; 100 mg) in 10 mL of pyridine. The resulting mixture was stirred under an atmospheric pressure of H2 at room temperature for 3 h. The reaction mixture was filtered through a pad of diatomaceous earth and concentrated in vacuo. Purification by radial chromatography (SiO2; 5% MeOH in CHCl3, saturated with NH4OH) gave 185 mg (0.354 mmol, 61%) of a yellow oil which was converted to the dioxalate salt according to the procedure described in Example 1, Part C.

Provenance & Evidence