Tri-o-tolylphosphine → 4-(3'-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

17.9 mg (19.55 μmol, 0.044 eq.) Pd2(dba)3 and 5.9 mg (19.38 μmol, 0.044 eq.) P(o-tolyl)3 were dissolved in 6 ml dry toluene. Then 58.9 mg (610 μmol, 1.39 eq.) NaOt-Bu was added, followed by a solution of 101 mg (442 μmol) 3-(S)-Isopropyl-piperazine-1-carboxylic acid tert-butyl ester (85) and 110 mg (445 μmol, 1.01 eq.) 1-Benzyl-3-bromo-benzene (87). The resulting mixture was heated at 100° C. for 19 h. After filtrating the reaction mixture through celite the solvent was evaporated. Column chromatography (hexanes/EtOAc (3+1)) yielded 39.6 mg (100 μmol, 22.71%) 4-(3′-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester (88).

Provenance & Evidence