tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Palladium acetate (65 mg, 0.29 mmol) and RuPhos (271mg, 0.58mmol) were dissolved in toluene (10 mL), degassed and purged with nitrogen and warmed to 50°C for 15 minutes. In a separate vessel, were mixed 3-bromo-2-methyl pyridine (1.00g, 5.81 mmol), BOC-piperazine (1.08g, 5.81mmol), sodium tertbutoxide and toluene (17 mL). The mixture was degassed, purged with nitrogen and warmed to 50°C. The catalyst was transferred to the reaction vessel and the mixture degassed and purged with nitrogen. The reaction was heated at 100°C overnight under nitrogen. The mixture was filtered through GF/F paper, washing with MeOH. The filtrate was concentrated to provide a dark brown gum. The gum was purified by flash silica chromatography, elution gradient 30 to 80% EtOAc in heptane. Pure fractions were evaporated to provide the desired product as a gum (1.492g, 93%). Rf (1:1 EtOAc/heptane) 0.3

Provenance & Evidence