Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the Multipin™ approach

doi:10.1023/A:1009642429617

Paper

Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the Multipin™ approach

Published 2004 · C. Bui, A. M. Bray, Y. Pham

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Abstract

The 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid (Barany)linker and its monomethoxy analog were applied to theMultipin™ method of solid phase synthesis. Acomparative assessment of reductive amination and cleavage ofthese linkers under conditions of multiple synthesis indicatedthat both were applicable to a broad range of primary aminesincluding aniline and 4-nitroaniline. Apart from the greaterlability of the dimethoxy version under TFA cleavage, there wasno observable advantage of one linker over the other within thedescribed experiment.

Study Snapshot

Both 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid (Barany) and its monomethoxy analog are applicable to a broad range of primary amines using the MultipinTM method, with no observable advantage of one over the other.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the Multipin™ approach

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References

Citations

TiCl(OiPr)3 and NaBH(OAc)3: an efficient reagent combination for the reductive amination of aldehydes by electron-deficient amines

TiCl(OiPr)3 and NaBH(OAc)3 effectively reductively aminate aldehydes by electron-deficient amines, yielding secondary amines in good yields.

Solid-phase synthesis of an N-(phenylalkyl)cinnamide library via Horner-Wadsworth-Emmons reaction.

This study presents a novel, automated solid-phase approach for the synthesis of diverse N-(phenylalkyl)cinnamides, analogues of the NR2B antagonist 2, using polymer supported N-(phenylalkyl)amines, (diethylphosphon

Solid-phase versus solution synthesis of asymmetrically disubstituted furazano[3,4-b]pyrazines

Solid-phase synthesis of asymmetrically disubstituted furazano[3,4-b]pyrazines allows for easier preparation without selectivity issues compared to solution chemistry.