Rolipram, (±)-4-(3-cyclopentyloxyl-4-methoxylphenyl)-2-pyrrolidinone,is known as a potent and selective inhibitor of phosphodiesterase type Ⅳ(PDE Ⅳ)1.In fact, although both enantiomers are active, the levorotatory isomer, for which several synthesis has been recently reported2, has proved to be the most active one. Hashimoto and Jung have repored rolipram's synthesis via intramolecular C-H insertion reaction of α -methoxylcarbonyl- α -diazoacetamide and α-phenylsulfonyl-α-diazoacetamide3,4. Based on the discovery of the excellent N-protecting group:cumyl, we have now explored a new and facile route to 1