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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51Cyclic Precursors
is known as the Schmidt reaction.
48
The general procedure uses sodium azide in an
acidic medium to generate hydrazoic acid. As with the Beckmann rearrangement,
the lactam products can be hydrolyzed to the corresponding amino acid. When 2-iso-
butylcyclopentanone (71) was reacted with polyphosphoric acid and sodium azide,
5-isobutyl-2-piperidone (72) was obtained.
49
Acid hydrolysis gave a near-quantitative
yield of 7-methyl-5-aminooctanoic acid (73). In general, the rearrangement leads to
attachment of nitrogen to the more highly substituted carbon of the cyclic ketone.
N
CO
2
H
NH
2
O
O
H
NaN
3
, PPA
50°C, 18 h
12% HCl
reux, 14 h
72
7371 ...
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