N-CINNAMOYLPROLINE DERIVATIVE AS NEW OPTICALLY RESOLVING AGENT AND ITS ALKALI SALT

PURPOSE:To obtain a new optically resolving agent useful for resolving a raw material for producing a medicine, containing N-cinnamoylproline derivatives and their salt most of which are new compounds. CONSTITUTION:A new optically active resolving agent selected from N- cinnamoylproline derivatives of formula I (R H or lower alkyl; R is H, halogen, hydroxy, nitro, lower alkoxy, lower alkyl or phenyl which may be substituted; R is hydroxy or reactive residue) or its alkali salt. Among compounds of formula I, compounds except a compound wherein R and R are H at the same time are all new compound. The optically resolving agent of formula I is effective for optical resolution of a racemic modification having a structure capable of possessing pi-pi mutual action on a cinnamoyl part, such as an N-substituted-3-hydroxymethyl-5-nitro-2,3-dihydroindole. The compound of formula I is obtained by reacting an (S)- or (R)-proline derivative of formula II with a cinnamoyl derivative of formula III in the presence of a base.