2-Bromoanisole → HCID 178418215, compound

Participants

Reaction Conditions

Reaction Steps

TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.046 g, 0.05 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.063 g, 0.10 mmol) were mixed together and evacuated and purged with nitrogen 3 times. toluene (24.91 ml) was added and the resulting mixture heated to 50°C for 10 minutes. In a second reaction vessel was mixed sodium tert-butoxide (0.387 g, 4.03 mmol), (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.500 g, 2.52 mmol), 1-bromo-2-methoxybenzene (0.314 ml, 2.52 mmol) and toluene (24.91 ml). The mixture was evacuated and purged with nitrogen 3 times. The solution of catalyst was added to the reaction mixture and the resulting mixture was heated at 105 °C for 16 hours. The reaction mixture was cooled to RT and filtered through celite and evaporated. The crude product was purified by flash silica chromatography, elution gradient 100% DCM. Pure fractions were evaporated to dryness to afford (1S,4S)-tert-butyl 5-(2-methoxyphenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.529 g, 68.9 %) as a yellow gum.

Provenance & Evidence