Synthesis of Enantiomerically Pure N-Acyl Amino Nitriles via Catalytic Dehydration of Oximes and Application in a de Novo Synthesis of Vildagliptin

Rommelmann P, Betke T, Gröger H (2017)
Organic Process Research & Development 21(10): 1521-1527.

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Abstract
An alternative route toward enantiomerically highly enriched N-acyl amino nitriles based on the Cu(OAc)(2)-catalyzed dehydration of aldoximes, which are readily available from N-acyl L- or D-alpha-amino aldehydes through condensation with hydroxylamine, has been developed. The desired products were obtained with high conversion and in enantiomeric excesses of 97-99% ee. Furthermore, this method has been applied in the synthesis of an N-chloroacetylated 2-cyanopyrrolidine, which represents a building block for the synthesis of Vildagliptin.
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Rommelmann P, Betke T, Gröger H. Synthesis of Enantiomerically Pure N-Acyl Amino Nitriles via Catalytic Dehydration of Oximes and Application in a de Novo Synthesis of Vildagliptin. Organic Process Research & Development. 2017;21(10):1521-1527.
Rommelmann, P., Betke, T., & Gröger, H. (2017). Synthesis of Enantiomerically Pure N-Acyl Amino Nitriles via Catalytic Dehydration of Oximes and Application in a de Novo Synthesis of Vildagliptin. Organic Process Research & Development, 21(10), 1521-1527. doi:10.1021/acs.oprd.7b00169
Rommelmann, P., Betke, T., and Gröger, H. (2017). Synthesis of Enantiomerically Pure N-Acyl Amino Nitriles via Catalytic Dehydration of Oximes and Application in a de Novo Synthesis of Vildagliptin. Organic Process Research & Development 21, 1521-1527.
Rommelmann, P., Betke, T., & Gröger, H., 2017. Synthesis of Enantiomerically Pure N-Acyl Amino Nitriles via Catalytic Dehydration of Oximes and Application in a de Novo Synthesis of Vildagliptin. Organic Process Research & Development, 21(10), p 1521-1527.
P. Rommelmann, T. Betke, and H. Gröger, “Synthesis of Enantiomerically Pure N-Acyl Amino Nitriles via Catalytic Dehydration of Oximes and Application in a de Novo Synthesis of Vildagliptin”, Organic Process Research & Development, vol. 21, 2017, pp. 1521-1527.
Rommelmann, P., Betke, T., Gröger, H.: Synthesis of Enantiomerically Pure N-Acyl Amino Nitriles via Catalytic Dehydration of Oximes and Application in a de Novo Synthesis of Vildagliptin. Organic Process Research & Development. 21, 1521-1527 (2017).
Rommelmann, Philipp, Betke, Tobias, and Gröger, Harald. “Synthesis of Enantiomerically Pure N-Acyl Amino Nitriles via Catalytic Dehydration of Oximes and Application in a de Novo Synthesis of Vildagliptin”. Organic Process Research & Development 21.10 (2017): 1521-1527.
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