Tetrabutylammonium Fluoride → 1-(4-Tert-butylphenyl)-2,5-bis(4-ethynylphenyl)pyrrolidine

Participants

Reaction Conditions

Reaction Steps

Dissolved the product of Example 105A (322 mg, 0.588 mmol) in anhydrous THF (5 mL) under nitrogen, added 1M TBAF in THF (1.322 mL, 1.322 mmol), and stirred at 25° C. for 30 min. The reaction darkened immediately upon addition and remained a brown color throughout the reaction. Removed solvent by rotary evaporation, dissolved the residue in 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 (289 mg). Purified by flash chromatography (silica gel, 3.8 cm×14 cm, 20% CH2Cl2/hexanes) to the title compound as a light yellow foam (176 mg, 74%) as a mixture of stereoisomers. MS (ESI+) m/z 404 (M+H)+.

Provenance & Evidence