Binol → HCID 58181232, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,4-diiodobenzene (9.98 g, 30.3 mmol), tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (2.0 g, 10.1 mmol), copper (I) iodide (434 mg, 3.03 mmol), 1,1′-bi-2-naphthol (867 mg, 3.03 mg), tripotassium phosphate (5.14 g, 24.2 mmol) and anhydrous N,N-dimethylformamide (50 ml) was stirred at 80° C. for 2 days. 1,4-Diiodobenzene (3.33 g, 10.1 mmol) was added, and the mixture was stirred at 90° C. overnight. After cooling to room temperature, the mixture was filtered through Celite, and the insoluble material was washed with ethyl acetate. The filtrate and washing solution were combined, and the mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography (ethyl acetate:hexane=80:20) to, give tert-butyl 5-(4-iodophenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1.34 g, yield 33%).

Provenance & Evidence