Kilogram scale teneligliptin hydrobromide, a DPP-4 inhibitor, was synthesized by amination reduction, de-protection, salt formation, and crystallization using (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylicacid tert-butyl ester (Ⅱ) and 1-(3-methyl-1-phenyl-1H-pyrazole-5-yl) piprazine (Ⅲ) as raw materials, sodium triacetoxyborohydride as reducing agent and only toluene as solvent. The structure and properties of the product were characterized by FTIR, LC-MS, XRD, 1HNMR and polarimeter. The optimum synthetic conditions of amination reduction, de-protection and salt formation were as follows: n(Ⅱ)∶n(Ⅲ)∶n(V)=1.0∶1.0∶1.5, and reaction time 2~3 h. Under these conditions, the purity of obtained the product 3-({(2S,4S)-1-tert-butoxycarbonyl-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1-piperazinyl]-2-pyrrolidinyl}formyl) thiazolidine (Ⅳ) with the of 98.40%; n(Ⅱ)∶n(Ⅲ)∶n(HBr)=1.0∶1.0∶3.5, reaction time 4 h and crystallized at 0~5 ℃ with the total yield of 88.33% and the purity of 99.95%, []20D=-32.5°.