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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 10
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Original Articles

1-Phenyl-2-pyrrolidinyl-cyclopentylamine via Thermal Rearrangement

Babu G. Sundar Department of Medicinal Chemistry, Worldwide Discovery Research, Cephalon, Inc., West Chester, Pennsylvania, USACorrespondence[email protected]
,
Kurt Josef Department of Medicinal Chemistry, Worldwide Discovery Research, Cephalon, Inc., West Chester, Pennsylvania, USA
,
Robert McHugh Department of Medicinal Chemistry, Worldwide Discovery Research, Cephalon, Inc., West Chester, Pennsylvania, USA
&
Curtis Haltiwanger Department of Pharmaceutics, Worldwide Drug Development, Cephalon, Inc., West Chester, Pennsylvania, USA
Pages 1481-1485 | Received 04 Feb 2010, Published online: 30 Mar 2011
 
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Abstract

Thermal rearrangement of aminoimine, 1, followed by hydrogenation produced 1-phenyl-2-pyrrolidinyl cyclopentylamine 3. The structure and stereochemistry of this novel amine 4 was identified by x-ray crystallography of the 2-chloro-6-iodo-nicotinamide derivative as a hydrogen maleate salt.

ACKNOWLEDGMENTS

The authors thank Ed Bacon for his support and encouragment. Thanks go to Dr. Amy Sarjeant (JHU X-ray data collection) and Torsten Herbertz (Molecular Modeling and Computational Science) for their help.

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