Asymmetric synthesis method, related raw material and preparation method of (S,S)-2,8-diazabicyclo[4,3,0]nonane

摘要

The present invention relates to an asymmetric synthesis method of a chiral intermediate (S,S)-2,8-diazabicyclo[4,3,0]nonane (I) of moxifloxacin, wherein an imide or enamine compound is obtained by dehydration reaction of the pyrrolidine-3-ketone as shown in formula (II) and chiral amine(R)-1-phenylethylamine, followed by the reduction of the imide or enamine compound to obtain a compound of formula (III) or (IV) having the chiral structure of formula (I), and then a compound of formula (I) is obtained by intramolecular cyclization, and removal of the chiral auxiliary group and amino-protecting group. The present invention also relates to pyrrolidine-3-ketone as shown in formula (II) and a preparation method therefor,;and in the formula (I), (II), (III), (IV), R is an amino-protecting group, especially C1-4 alkoxycarbonyl, benzyloxycarbonyl or benzyl which can be removed by hydrolysis or hydrogenation. Z═H2 or O; when Z═H2, Y is chlorine, bromine, iodine, methanesulfonate, tosylate, hydroxyl or hydroxyl with protection; and when Z═O, Y is OR1, and R1 is C1-4 alkyl.

主权项

1. A compound which has a structural formula as shown in formula (IIa), wherein, R is an amino-protecting group selected from the group consisting of C1-4 alkoxycarbonyl, benzyloxycarbonyl and benzyl which can be removed by hydrolysis or hydrogenation; Y is one of chlorine, bromine, iodine, methanesulfonate, tosylate, or hydroxyl.