Enzymes are versatile biocatalysts and find increasing application in many areas, including organic synthesis. The major advantages of using enzymes in biotransformations are their chemo-, regio-, and stereoselectivity as well as the very mild reaction conditions that can be used, where the generation of the side products is minimized. The synthesis of optically pure compounds is increasingly in demand in the pharmaceutical, fine chemicals, cosmetic, and agroalimentary industries. Undoubtedly, the complete transformation of a racemic mixture of amine or alcohols into a single enantiomer is of the challenging problems in chiral synthesis. The lipase catalyzed the enantioselective transesterification of S-arylamine, whereas the Pd nanoparticles catalyzed the racemization of unreacted R-enantiomer. The optimized process was then applied on the readily available rac-1,2,3,4-tetrahydro-1-naphthylamine to obtain the key chiral building block subsequently used in the new synthesis of target drug.