Synthesis of alpha-aminonitriles

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

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260464, 260465D, 260465E, 2604655R, 546330, 548342, 549 74, 549492, C07D29514, C07C12178

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045515263

ABSTRACT:
Described is a process for preparing alpha-aminonitriles having the formula ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.7 -C.sub.15 aralkyl, unsubstituted or substituted aryl or heteroaryl or alternatively, R.sub.1 and R.sub.2 together with the carbon atom form a 3 to 12 member cycloalkyl group, or with a heteroatom form a 3 to 12 member heterocyclic group and R.sub.3 and R.sub.4 together with the nitrogen atom form a 3 to 12 member heterocyclic group and R.sub.3 and R.sub.4 together with the nitrogen atom form a 3 to 12 member heterocyclic group, optionally including oxygen, sulfur, or phosphorus as a second heteroatom, the process comprising: reacting an aldehyde or a ketone with trimethylsilyl cyanide (solvent is optional) to prepare alpha-trimethylsilyloxynitrile; reacting the silyloxynitrile so formed with an amine (or ammonia) in the presence of a loweralkyl alcohol (or water) to prepare the desired alpha-aminonitrile.
The compounds so prepared are intermediates in the preparation of aminoacids.

REFERENCES:
Gassman et al., Tetrahedron Letters, No. 40, pp. 3773-3776 (1978).
Stout et al., J. Org. Chem., vol. 48, 5369 (1983).
Ojima et al., Chemistry Letters, pp. 331-334, 737-740 (1975).

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