Efficient asymmetric synthesis of ABT-594; a potent, orally effective analgesic

…, CN Hsiao, HE Morton, DA Dickman, W Arnold…

Index: Lynch, John K.; Holladay, Mark W.; Ryther, Keith B.; Bai, Hao; Hsiao, Chi-Nung; Morton, Howard E.; Dickman, Daniel A.; Arnold, William; King, Steven A. Tetrahedron Asymmetry, 1998 , vol. 9, # 16 p. 2791 - 2794

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Citation Number: 38

Abstract

A concise asymmetric synthesis of (R)-2-chloro-5-(2-azetidinylmethoxy) pyridine (ABT-594) is presented in which the key intermediate t-butoxycarbonyl protected (2R)-azetidinylalcohol is obtained in three steps from the dibenzyl ester of D-aspartic acid in 44% yield and> 99% ee.