
139Biologically Important Amino Acids
CO
2
Et
F
CO
2
Et
F F
CO
2
F F
2
2
reux
cat. p-TsOH
3
2N HCl/MeOH
2. 1N HCl
3. H
2
78 79 80
68%
30%
2-Pyrrolidinone derivatives are useful synthons for the preparation of 4-ami-
nobutanoic acid derivatives of all types. Ethyl pyroglutamate (81), derived from
L-glutamic acid, was converted to cyanomethyl-2-pyrrolidinone 82.
113
Reduction to
the amine and Cope elimination
114
gave 83, which was hydrolyzed to 4-aminohex-5-
enoic acid (84; known as vigabatrin). It is known that 84 is an irreversible inhibitor
of GABA-T. Due this mode of action, vigabatrin has been shown to increase levels
of GABA in t