The heterogeneous catalytic hydrogenation of (S)-N-(t-butyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide was carried out over supported metal catalysts. Except for Pt, all the catalysts were very selective toward the formation of (3S, 4aS, SaS)-N-(t-butyl)decahydro-3-isoquinolinecarboxamide. However, Pd and Ni catalysts deactivated fairly quickly, while Ru and Rh did not deactivate at all for more than 100 h. Among these catalysts, Ru showed the best performance. The high diastereoselectivity was assumed to be the result of the rigidity of the appended chiral group which helps the preferential adsorption of the reactant in one direction.