In this paper we present a new approach in the study of aorto-coronaric bypass anastomoses configurations. The theory of optimal control based on adjoint formulation is applied in order to optimize the shape of the zone of the incoming branch of the bypass (the toe) into the coronary. The aim is to provide design indications in the perspective of future development for prosthetic bypasses. With a reduced model based on Stokes equations and a vorticity functional in the down field zone of bypass, a Taylor-like patch is found. A feedback procedure with Navier-Stokes fluid model is proposed based on the analysis of wall shear stress and its related indexes such as OSI.