الفهرس 
Preparation of Racemic ?-amino NitrilesOnly 14 pages are availabe for public view
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Abstract
The thesis includes an introduction reviewing the methods for preparations and
asymmetric transformations of α -amino nitriles and α-amino acids.
The thesis describes the preparation of racemic α-amino nitriles 1-10 as starting
materials.
General formula of racemic α-amino nitriles
The α-p-fluorobenzylamino nitriles 1-5 and 9 were easily synthesized with
high yields (81- 90 %) by treating a methanolic solution containing equimolar
amounts of the respective carbonyl compound, KCN, and benzylamine with
ultrasonic irradiation in the presence of a catalytic amount of acetic acid.C O
R1
H
+ + KCN
MeOH/ AcOH
Ultrasound
-H2O/KOAc
R1= Ph, Ar, Alk
H2N R2 CH
CN
R1
H
N R2
R2= -CH2-C6H4-F
Scheme 1. Preparation of racemic α-amino nitriles
English Summary
II
The utilization of ultrasound for the synthesis of compounds 6-8 and 10
proved impractical due to the formation of unidentified byproducts. Instead, a
more convenient approach, following the Texier-Baullet method, was employed
for the synthesis of α-amino nitriles 6-8 and 10.C O
R1
H
+ H2N R2
Al2O3/ CH2Cl2
-H2O
C
R1
H
N R2
1) TMSCN / AlCl3
2) H+ / H2O
3) NaHCO3
R2= Bn, i-Pr
R1= 4-Me-C6H4 , C14H11
CH
CN
R1
H
N R2
Scheme 2: Synthesis of amino nitriles 6-8 and 10
In this procedure, the carbonyl compounds were initially transformed into
Schiff bases using isopropylamine and aluminum oxide. Subsequent treatment
with trimethylsilyl cyanide under AlCl3 catalysis, followed by hydrolysis,
resulted in the production of products with a yield of 74-79 %.
Treatment of racemic (p-fluorobenzylamino)tolylacetonitrile 4 with (R)-(-)
mandelic acid as a chiral auxiliary in presence of a small amount of ethanol below
0oC resulted in a spontaneous and almost quantitative (91%) precipitation of the
crystalline amygdalate. It is assumed that the salt consists of equal amounts of the
two diastereoneric forms 11’ and 11”, respectivel