871258-03-6Relevant articles and documents
Regiospecific functionalization of pharmaceuticals and other biologically active molecules through cyclopalladated compounds. 2-iodination of phentermine and L-tryptophan methyl ester
Vicente, Jose,Saura-Llamas, Isabel,Bautista, Delia
, p. 6001 - 6004 (2008/10/09)
Phentermine hydrochloride ((PhCH2CMe2NH 3)Cl) or L-tryptophan methyl ester hydrochloride ([C 8H6NCH2CH(CO2Me)NH3]Cl) reacts with Pd(OAc)2 in a 1:1 molar ratio to give the cyclometalated complex [Pd2(k2-C,N-C6H4CH 2CMe2NH2-2)2(μ-Cl)2] (1) or (S,S)-[Pd2{K2-C,N-C8H 5NCH2CH(CO2Me)NH2-2} 2(μ-Cl)2] (2), respectively. Reaction of 1 or 2 with iodine affords trans-[PdCl2(NH2CMe2CH 2C6H4I-2)2] (3) or trans-(S,S)-[PdCl2{NH2CH(CO2Me)CH 2C8H5NI-2)2] (4), which further reacts with 1,10-phenanthroline to give [PdCl2(phen)] and the free amine 2-I-phentermine (5) or (S)-2-I-tryptophan methyl ester (6) (overall yields 44 and 51%, respectively, considering phentermine and L-tryptophan methyl ester as starting materials). The crystal structure of complex 3 has been determined by X-ray diffraction studies.