A Short, Efficient Synthesis of the Novel Cholinergic Channel Activator, ABT 418, from L-Proline

Richard L. Elliott; Hana Kopecka; Nan-Horng Lin; Yun He; David S. Garvey

doi:10.1055/s-1995-4014

Synthesis 1995; 1995(7): 772-774
DOI: 10.1055/s-1995-4014

short paper

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A Short, Efficient Synthesis of the Novel Cholinergic Channel Activator, ABT 418, from L-Proline

Richard L. Elliott^* , Hana Kopecka, Nan-Horng Lin, Yun He, David S. Garvey

^*Neuroscience Research, Pharmaceutical Products Division, Abbott Laboratories, Abbott Park, Illinois 60064, USA, Fax +1(708)9386603

Abstract

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A short and efficient synthesis of the novel cholinergic channel activator ABT 418, (S)-3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole, has been developed. The four-step route from L-proline afforded the target compound in ca. 35% overall yield in very high chemical and enantiomeric purity. This route has afforded multigram quantities of the clinical candidate and should be amenable to kilogram-scale reactions.

ABT 418 was synthesized in four steps (35% yield) from (L)-proline

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