An optically active N-protected azetidine-2-carboxylic acid (5) can be
produced by preparing an optically active 4-amino-2-halobutyric acid (3)
by halogenating an optically active 3-hydroxy-2-pyrrolidinone (1) with
inversion of configuration to prepare an optically active
3-halo-2-pyrrolidinone (2) followed by hydrolysis or by halogenating an
optically active 4-amino-2-hydroxybutyric acid ester (6) with inversion
of configuration to prepare an optically active 4-amino-2-halobutyric
acid ester (7) followed by hydrolysis or by halogenating the compound (6)
with inversion of configuration to prepare the compound (7), cyclizing
the same to prepare the compound (2) followed by hydrolysis, further
cyclizing the compound (3) followed by treating the reaction product with
an amino group-protecting agent. The thus-obtained compound (5) can be
improved its optical purity further by recrystallization ##STR00001##