Ammonium Hydroxide → HCID 46205771, compound

Participants

Reaction Steps

To a solution of N-BOC-pyrrolidine (3.0 mL, 17.1 mmol) and (−)-sparteine (3.9 mL, 17.1 mmol) in tert-butyl methyl ether (36 mL) at −78° C. was added sec-butyl lithium (1.4 M solution in cyclohexane, 12.21 mL, 17.1 mmol) and the mixture stirred at <−70° C. for 3 hours. A solution of zinc (II) chloride (1M solution in diethyl ether, 10.2 mL, 10.2 mmol) was added, the mixture stirred at −78° C. for 30 minutes and then warmed to ambient temperature. The mixture was stirred for 30 minutes and EXAMPLE 50A (3.32 g, 14.25 mmol), t-butylphosphine-tetrafluoroboric acid (249 mg, 0.855 mmol) and palladium (II) acetate (153 mg, 0.69 mmol) were added and the mixture stirred at ambient temperature overnight. Concentrated ammonium hydroxide (1 mL) was added and the mixture stirred at ambient temperature for 30 minutes. Insoluble material was filtered through Celite and washed with ethyl acetate. The filtrate was washed with 0.5 M hydrochloric acid and water and concentrated. The residue was purified by flash chromatography on silica gel, using a gradient of 10-30% ethyl acetate in hexane to give the title compound (2.66 g).

Provenance & Evidence