An alternative synthesis of the CNS stimulant Prolintane

Mujahid, Mohammad; Korpe, Gajanan V.; Deshmukh, S. P.; Bhadange, S. G.; Muthukrishnan, M.

doi:10.24820/ark.5550190.p010.952

Arkivoc

2019

DOI: 10.24820/ark.5550190.p010.952

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An alternative synthesis of the CNS stimulant Prolintane

Mohammad Mujahid¹,

Gajanan V. Korpe²,

S. P. Deshmukh³

et al.

Abstract: An alternative synthesis of prolintane, a CNS stimulant, is reported using commercially available allylbenzene in good overall yield (32.3%). The key transformations include epoxidation, Grignard reaction, Mitsunobu and reduction protocols. N Prolintane Five StepsOverall Yield-32.3% Allyl benzene

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Cited by 3 publications

References 8 publications

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Multicomponent Synthesis of α-Branched Amines via a Zinc-Mediated Carbonyl Alkylative Amination Reaction

Phelps,

Kumar,

Robinson

et al. 2024

J. Am. Chem. Soc.

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Methods for the synthesis of α-branched alkylamines are important due to their ubiquity in biologically active molecules. Despite the development of many methods for amine preparation, C(sp 3 )-rich nitrogen-containing compounds continue to pose challenges for synthesis. While carbonyl reductive amination (CRA) between ketones and alkylamines is the cornerstone method for α-branched alkylamine synthesis, it is sometimes limited by the sterically demanding condensation step between dialkyl ketones and amines and the more restricted availability of ketones compared to aldehydes. We recently reported a "higher-order" variant of this transformation, carbonyl alkylative amination (CAA), which utilized a halogen atom transfer (XAT)mediated radical mechanism, enabling the streamlined synthesis of complex α-branched alkylamines. Despite the efficacy of this visible-light-driven approach, it displayed scalability issues, and competitive reductive amination was a problem for certain substrate classes, limiting applicability. Here, we report a change in the reaction regime that expands the CAA platform through the realization of an extremely broad zinc-mediated CAA reaction. This new strategy enabled elimination of competitive CRA, simplified purification, and improved reaction scope. Furthermore, this new reaction harnessed carboxylic acid derivatives as alkyl donors and facilitated the synthesis of α-trialkyl tertiary amines, which cannot be accessed via CRA. This Zn-mediated CAA reaction can be carried out at a variety of scales, from a 10 μmol setup in microtiter plates enabling high-throughput experimentation, to the gramscale synthesis of medicinally-relevant compounds. We believe that this transformation enables robust, efficient, and economical access to α-branched alkylamines and provides a viable alternative to the current benchmark methods.

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Multicomponent Synthesis of α-Branched Amines via a Zinc-Mediated Carbonyl Alkylative Amination Reaction

Phelps,

Kumar,

Robinson

et al. 2024

J. Am. Chem. Soc.

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show abstract

Synthesis of the Central Nervous System Stimulant Prolintane

Fatima Zeenath,

Rao,

Annapurna

et al. 2024

Organic Preparations and Procedures International

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Base-mediated alternate route for multi-functionalized allylbenzenes using ring transformation strategy

Shetgaonkar

Singh

2020

Synthetic Communications

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An alternative synthesis of the CNS stimulant Prolintane

Cited by 3 publications

References 8 publications

Multicomponent Synthesis of α-Branched Amines via a Zinc-Mediated Carbonyl Alkylative Amination Reaction

Multicomponent Synthesis of α-Branched Amines via a Zinc-Mediated Carbonyl Alkylative Amination Reaction

Synthesis of the Central Nervous System Stimulant Prolintane

Base-mediated alternate route for multi-functionalized allylbenzenes using ring transformation strategy

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