Diisopropylamine → (2R)-1-[2-(5-bromo-1-benzofuran-2-yl)ethyl]-2-methylpyrrolidine

Participants

Reaction Steps

4-Bromo-2-iodophenol (2.99 g, 90% pure, 9 mmol), palladium (II) acetate (112 mg, 0.50 mmol), triphenylphosphine (262 mg, 1.0 mmol), copper(I) iodide (571 mg, 3.0 mmol), and diisopropylamine (14 mL, 100 mmol) were dissolved into a 0.09 M MeCN solution of (R)-1-but-3-ynyl-2-methylpyrrolidine (120 mL, 10.8 mmol) and stirred at room temperature three days, then at 80° C. overnight. The reaction mixture was cooled to room temperature, concentrated, and chromatographed through a short column of silica with 2:1 hexanes/CH2Cl2 followed by a 0 to 1% gradient of MeOH/CH2Cl2. The appropriate fractions were concentrated, and the residue extracted with MeOH. The extracts were concentrated and partitioned between CH2Cl2 and 1 M aqueous Na2CO3, worked up as usual, dried (Na2SO4), and concentrated to provide the title compound as a dark red syrup (26% yield).

Provenance & Evidence