The development of hollow fiber reactor system for the production of chiral 1,2-epoxy-7-octence by epoxide hydrolase for Rhodotorula glutinis was investigated. Dodecane with high solubility of the racemic substrate passed through the lumen side of the hollow fiber reactor and cell suspension was recirculated through the shell side. The 2nd hollow fiber reactor was coupled to the production reactor to extract the diol byproduct which was the inhibitor of epoxide hydrolase. Optically pure (S)-1,2-epoxy-7-octene (0.6 M in dodecane) could be obtained using hollow-fiber reactor system.