tert-Butyl piperazine-1-carboxylate → 4-(2-Fluoro-naphthalen-1-yl)-piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A third intermediate compound, 1-(2-Fluoro-naphthalen-1-yl)-piperazine, was produced as follows: A solution of Pd(OAc)2 (44.8 mg, 0.2 mmol) and 2-(dicyclohexylphosphino)biphenyl (70.0 mg, 0.2 mmol) was degassed by bubbling N2 for 20 min. 1-Bromo-2-fluoro-naphthalene (0.448 g, 2 mmol) and 1-Boc-piperazine (0.446 g, 2.4 mmol) were added followed by the addition of NaOtBu (0.27 g, 2.8 mmol). The mixture was warmed up to 80° C. and kept at this temperature for 16 h. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel to give 4-(2-fluoro-naphthalen-1-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.24 g, 40%).

Provenance & Evidence