Tetrahydrofuran → 1-(4-Tert-butylphenyl)-2,5-bis(4-((trimethylsilyl)ethynyl)phenyl)pyrrolidine

Participants

Reaction Steps

To an oven-dried microwave tube (Size M, 5 mL) purged with nitrogen, added the product of Example 42C (340 mg, 0.662 mmol), bis(triphenylphosphine)palladium(II) dichloride (18.60 mg, 0.026 mmol), THF (2 mL), and triethylamine (2 mL). Stirred at room temperature for 5 min, then added copper(I) iodide (2.52 mg, 0.013 mmol), stirred the yellow mixture for 2 min, then nitrogen bubbled through for 15 min. Added trimethylsilylacetylene (0.374 mL, 2.65 mmol), sealed the tube with an aluminum crimp cap, and heated in an oil bath at 70° C. for 20 hr. Cooled the reaction to room temperature, added fresh bis(triphenylphosphine)palladium(II) dichloride (18.60 mg, 0.026 mmol) and copper(I) iodide (2.52 mg, 0.013 mmol), added additional trimethylsilylacetylene (0.374 mL, 2.65 mmol), and continued heating at 80° C. for 24 hr. Cooled the reaction to room temperature, diluted with Et2O (50 mL), washed with H2O (2×25 mL) and brine (25 mL), dried the organic phase over anhydrous MgSO4, filtered, and concentrated by rotary evaporation to a light tan foam (470 mg). Purified by flash chromatography (silica gel, 2.5 cm×10 cm, 2% Et2O/hexanes) to afford the title product as a yellow foam (324 mg, 89%) as a mixture of stereoisomers. MS (ESI+) m/z 548 (M+H)+.

Provenance & Evidence