可扩展合成与分离1-氨基-3-(4-溴苯基)环戊烷羧酸甲酯的四种立体异构体，它们是合成S1P1受体激动剂的有用中间体。
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.
作者信息
Wallace Grier A, Gordon Thomas D, Hayes Martin E, Konopacki Donald B, Fix-Stenzel Shannon R, Zhang Xiaolei, Grongsaard Pintipa, Cusack Kevin P, Schaffter Lisa M, Henry Rodger F, Stoffel Robert H
机构信息
Abbott Bioresearch Center, Medicinal Chemistry Department, 381 Plantation Street, Worcester, Massachusetts 01605, USA.
出版信息
J Org Chem. 2009 Jul 3;74(13):4886-9. doi: 10.1021/jo900376b.
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.
1-氨基-3-(4-溴苯基)环戊烷羧酸甲酯的各个异构体是合成S1P1受体激动剂的有用中间体。在此，我们描述了一种可扩展的合成方法，能够以克级规模分离该化合物的四种立体异构体，其对映体过量（ee）和非对映体过量（de）均大于98%。通过七步合成((1R,3R)-1-氨基-3-(4-辛基苯基)环戊基)甲醇，总产率为11%，ee和de均大于98%，证明了该方法的实用性。
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