1-(5-bromo-2-methoxyphenyl)pyrrolidine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a −78° C. solution of 1-(5-bromo-2-methoxy-phenyl)-pyrrolidine (270 mg, 1.1 mmol) in THF (17 mL) was added dropwise a solution of t-BuLi (1.3 mL, 1.7 M solution in pentane, 2.2 mmol). The resultant yellow solution was stirred for 30 min, treated with additional t-BuLi (1.3 mL, 1.7 M solution in pentane, 2.2 mmol), stirred for 45 min, and treated dropwise with 2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (0.8 mL, 4.4 mmol). The reaction was allowed to slowly warm to room temperature, stirred at room temperature overnight, and partitioned between saturated NH4Cl and EtOAc. The combined organic phases were dried with Na2SO4 and concentrated to give a tan oil. The crude product was purified by flash chromatography using 25 g of silica gel and 0-50% EtOAc in hexanes as eluant to afford 120 mg (35%) of 1-[2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyrrolidine as a white solid. M+H 304. stirred for 45 min stirred at room temperature overnight partitioned between saturated NH4Cl and EtOAc The combined organic phases were dried with Na2SO4 concentrated to give a tan oil The crude product was purified by flash chromatography