Scalable Synthesis and Isolation of the Four Stereoisomers of Methyl 1-Amino-3-(4-bromophenyl)cyclopentanecarboxylate, Useful Intermediates for the Synthesis of S1P1 Receptor Agonists

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• 作者：Grier A. Wallace ; Thomas D. Gordon ; Martin E. Hayes ; Donald B. Konopacki ; Shannon R. Fix-Stenzel ; Xiaolei Zhang ; Pintipa Grongsaard ; Kevin P. Cusack ; Lisa M. Schaffter ; Rodger F. Henry ; Robert H. Stoff
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：July 3, 2009
• 年：2009
• 卷：74
• 期：13
• 页码：4886-4889
• 全文大小：146K
• 年卷期：v.74,no.13(July 3, 2009)
• ISSN：1520-6904

文摘

The individual isomers of methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate are useful intermediates for the synthesis of S1P1 receptor agonists. Herein we describe a scalable synthesis and isolation of each of the four stereoisomers of this compound in gram quantities with >98% ee and de. The utility of this approach is demonstrated by the synthesis of ((1R,3R)-1-amino-3-(4-octylphenyl)cyclopentyl)methanol in 7 steps, 11% overall yield, and >98% ee and de.