Synthesis of alpha-aminonitriles

Details Synthesis of alpha-aminonitriles Synthesis of alpha-aminonitriles

1984-09-26

1985-11-05

Torrence, Dolph H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

260465D, 260465E, 548561, 549 74, 549492, 556417, C07D21355, C07C12178

Patent

active

045515379

ABSTRACT:
Disclosed is a process for preparing optically active alpha-aminonitriles of the formula ##STR1## by the reaction of alpha-trimethylsilyloxynitriles with optically active alpha-methylbenzylamine in the presence of a loweralkyl alcohol.
In the above formula, R denotes C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.7 -C.sub.15 aralkyl or unsubstituted or substituted aryl or heteroaryl.
In general, R-alpha-methylbenzylamine gave I and III as the major and the minor products, respectively. Whereas, S-alpha-methylbenzylamine gave II and IV as the major and the minor products, respectively.
The compounds so prepared are intermediates in the preparation of optically active aminoacids.

REFERENCES:
Stout et al., J. Org. Chem., vol. 48, 5369, (1983).

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