Toluene → (1S,4S)-5-(5-Benzoyl-3-pyridyl)-2-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane

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Reaction Steps

In a sealed pressure tube under a nitrogen atmosphere, 3-benzoyl-5-bromopyridine (0.542 g, 2.1 mmol), (1S,4S)-N-(tert-butoxycarb- onyl)-2,5-diazabicyclo[2.2.1]heptane (0.475 g, 2.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.04 g, 0.04 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.05 g, 0.08 mmol), sodium tert-butoxide (0.380 g, 3.8 mmol) and anhydrous toluene (20 mL) were stirred at 90° C. for 20 h. The reaction mixture was cooled to room temperature and diluted with water (200 mL) and then extracted with diethyl ether (100 mL). The diethyl ether extract was dried (MgSO4), filtered and concentrated by rotary evaporation. The residue was purified by flash chromatography on silica gel, using a gradient of 50% to 80% ethyl acetate:hexane as eluent, to yield 0.364 g (48%) of a yellow oil.

Provenance & Evidence