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Strecker reaction

Aldrich ChemFiles 2006, 6.7, 10.

The one-pot synthesis of a-amino nitriles by reaction of an aldehyde, ammonia, and hydrogen cyanide is commonly known as the Strecker reaction.1 Recent modifications to the traditional Strecker reaction have seen the replacement of the cyanide source from toxic hydrogen cyanide to the comparatively mild trimethylsilyl cyanide.2,3 Ruthenium has also been demonstrated to catalyze the Strecker reaction.4

Sigma-Aldrich now offers a polymer-supported ruthenium complex to be used as a mild catalyst for the Strecker reaction.

Scheme 1

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Typical Experimental Procedure

Ethylenediaminetriacetic acid–ruthenium(III) chloride complex, polymerbound (15 mg, 0.005 mmol) was charged into a reaction vessel followed by the addition of acetonitrile (2.0 mL), the aldehyde (1.0 mmol), the amine (1.15 mmol), and trimethylsilyl cyanide (1.5 mmol). The resulting mixture was stirred at room temperature overnight, filtered, and the filtrate collected. The resin was washed with several portions of acetonitrile, and the filtrates combined and evaporated to dryness. The residue was purified by flash column chromatography (20 g of silica gel; 1.5 3 20 cm column; ethyl acetate:hexane 1:9 as eluent) to yield the desired product. The structures of the isolated products were confirmed by 1H NMR and mass spectrometry.

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Materials

     

References

  1. Strecker, A. Ann. Chem. Pharm. 1850, 75, 27.
  2. Yadav, 3,5-Dimethoxybenzaldehyde 86 92 51 J. S. et al. Tetrahedron 2004, 60, 1767.
  3. Mai, K.; Patil, G. Tetrahedron Lett. 1984, 25, 4583.
  4. De, S. K. Synth. Commun. 2005, 35, 653.

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