October 2013
Intermediate to advanced
242 pages
9h 22m
English
Content preview from Methods of Non-a-Amino Acid Synthesis, 2nd Edition
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96
Methods of Non-α-Amino Acid Synthesis, Second Edition
were prepared as potential irreversible inactivators of GABA transferase
24
(also see
Chapter 6, Section 6.2).
CO
2
H
CO
2
H
NH
2
N N
NH
2
CO
2
H
EtO
2
C
H
O
OH
H
OH
O
SOCl
2
. EtOH
reux
NaBH
4
LiCl
1. HCl
2. Dowex
30 31 32
THF
Silverman prepared 5S-hydroxymethyl-2-pyrrolidinone (31)
25
by essentially the
same route as shown above. Conversion of the hydroxymethyl group to a mesylate
was followed by its reduction to a methyl group with zinc and iodomethane, giv-
ing 5R-methyl-2-pyrrolidinone (33).
26
The 5S-methyl derivative was prepared in an
identical manner from D-glutamic acid. When 33 was heated with 6N HCl, ethyl
4R
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