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
| Autor: | Lisa M. Schaffter, Martin E. Hayes, Robert H. Stoffel, Grier A. Wallace, Donald B. Konopacki, Thomas D. Gordon, Pintipa Grongsaard, Shannon R. Fix-Stenzel, Kevin P. Cusack, Xiaolei Zhang, Rodger F. Henry |
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| Rok vydání: | 2009 |
| Předmět: |
Molecular Structure
Stereochemistry Chemistry Organic Chemistry Carboxylic Acids Stereoisomerism Cyclopentanes Chemical synthesis chemistry.chemical_compound Receptors Lysosphingolipid Structure-Activity Relationship Yield (chemistry) Molecule Structure–activity relationship Amine gas treating Methanol Enantiomeric excess |
| Zdroj: | The Journal of organic chemistry. 74(13) |
| ISSN: | 1520-6904 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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