Asymmetric Synthesis of a TRPV1 Antagonist via tert-Butanesulfinamide-Directed Reductive Amination with a Chromanone

An expedient asymmetric synthesis of TRPV1 antagonist 1 has been developed and demonstrated on multikilogram scale. The enabling route to 1 is detailed herein and characterized by the following key transformations: an aldol-cyclodehydration sequence to install the chromanone, and an auxiliary-mediat...

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Bibliographic Details
Published inOrganic process research & development Vol. 18; no. 2; pp. 303 - 309
Main Authors Bellizzi, Mary E, Bhatia, Ashok V, Cullen, Steven C, Gandarilla, Jorge, Kruger, Albert W, Welch, Dennie S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.02.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
POTENTIAL VANILLOID-1 ANTAGONISTS
KETONES
ALDEHYDES
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Summary:An expedient asymmetric synthesis of TRPV1 antagonist 1 has been developed and demonstrated on multikilogram scale. The enabling route to 1 is detailed herein and characterized by the following key transformations: an aldol-cyclodehydration sequence to install the chromanone, and an auxiliary-mediated diastereoselective reductive amination.
ISSN:1083-6160
1520-586X
DOI:10.1021/op400184f