2023
DOI: 10.1021/acscentsci.3c00556
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The Tungsten-Promoted Synthesis of Piperidyl-Modified erythro-Methylphenidate Derivatives

Jonathan D. Dabbs,
Megan N. Ericson,
Justin H. Wilde
et al.

Abstract: Due to its efficacy as a dopamine receptor agonist, methylphenidate (MPH) is of interest as a potential therapeutic for cocaine addiction. While numerous derivatives of MPH have been investigated for their potential medicinal value, functionalization of the piperidine ring has not been explored. The pyridine borane ligand in WTp(NO)(PMe 3 )(η 2 -pyBH 3 ) is dearomatized by the metal and can be elaborated to the analogous η 2 … Show more

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Cited by 2 publications
(2 citation statements)
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“…10 This experiment suggests that the asymmetric unit {WTp(NO)(PMe 3 )} stabilizes the transition state (II in Figure 5) of distal DHP complexes significantly more than for the proximal diastereomers. Attempts to oxidatively decomplex the 1-azatriene complex 18D using CAN, DDQ, or O 2 /silica were unsuccessful; 11,27 CAN and DDQ both resulted in observable degradation of the complex with no identifiable free organics, while O 2 /silica rendered only starting material.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
See 1 more Smart Citation
“…10 This experiment suggests that the asymmetric unit {WTp(NO)(PMe 3 )} stabilizes the transition state (II in Figure 5) of distal DHP complexes significantly more than for the proximal diastereomers. Attempts to oxidatively decomplex the 1-azatriene complex 18D using CAN, DDQ, or O 2 /silica were unsuccessful; 11,27 CAN and DDQ both resulted in observable degradation of the complex with no identifiable free organics, while O 2 /silica rendered only starting material.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…Attempts to oxidatively decomplex the 1-azatriene complex 18D using CAN, DDQ, or O 2 /silica were unsuccessful; , CAN and DDQ both resulted in observable degradation of the complex with no identifiable free organics, while O 2 /silica rendered only starting material.…”
Section: Resultsmentioning
confidence: 99%