Efficient synthesis of cis-2,6-di-(2-quinolylpiperidine)

Derong Ding; Linda P. Dwoskin; Peter A. Crooks

doi:10.1016/j.tetlet.2013.07.067

Efficient synthesis of cis-2,6-di-(2-quinolylpiperidine)

Derong Ding, Linda P. Dwoskin, Peter A. Crooks

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

An efficient synthesis of cis-2,6-di-(2-quinolylpiperidine) has been developed. The key steps involve Wittig reaction of N-Cbz-protected cis-piperidine-2,6-dicarboxaldehyde (3) with 2-(triphenylphosphinyl-methyl) quinoline bromide (4) and sequential removal of the N-Cbz group and double bond reduction. This synthetic procedure provides an efficient preparation for this useful norlobelane analogue.

Original language	English
Pages (from-to)	5211-5213
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2013.07.067
State	Published - Sep 18 2013

Bibliographical note

Funding Information:
The authors gratefully acknowledge support from NIH grant U01 DA13519 . The University of Kentucky holds patents on lobeline and the analogues described in the current work. A potential royalty stream to LPD and PAC may occur consistent with University of Kentucky policy.

Keywords

Lobelane
Norlobelane analogues
Quinlobelane
Swern oxidation
Wittig reaction
cis-2,6-Di-(2-quinolylpiperidine)

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.07.067

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title = "Efficient synthesis of cis-2,6-di-(2-quinolylpiperidine)",

abstract = "An efficient synthesis of cis-2,6-di-(2-quinolylpiperidine) has been developed. The key steps involve Wittig reaction of N-Cbz-protected cis-piperidine-2,6-dicarboxaldehyde (3) with 2-(triphenylphosphinyl-methyl) quinoline bromide (4) and sequential removal of the N-Cbz group and double bond reduction. This synthetic procedure provides an efficient preparation for this useful norlobelane analogue.",

keywords = "Lobelane, Norlobelane analogues, Quinlobelane, Swern oxidation, Wittig reaction, cis-2,6-Di-(2-quinolylpiperidine)",

author = "Derong Ding and Dwoskin, {Linda P.} and Crooks, {Peter A.}",

note = "Funding Information: The authors gratefully acknowledge support from NIH grant U01 DA13519 . The University of Kentucky holds patents on lobeline and the analogues described in the current work. A potential royalty stream to LPD and PAC may occur consistent with University of Kentucky policy.",

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AU - Ding, Derong

AU - Dwoskin, Linda P.

AU - Crooks, Peter A.

N1 - Funding Information: The authors gratefully acknowledge support from NIH grant U01 DA13519 . The University of Kentucky holds patents on lobeline and the analogues described in the current work. A potential royalty stream to LPD and PAC may occur consistent with University of Kentucky policy.

PY - 2013/9/18

Y1 - 2013/9/18

N2 - An efficient synthesis of cis-2,6-di-(2-quinolylpiperidine) has been developed. The key steps involve Wittig reaction of N-Cbz-protected cis-piperidine-2,6-dicarboxaldehyde (3) with 2-(triphenylphosphinyl-methyl) quinoline bromide (4) and sequential removal of the N-Cbz group and double bond reduction. This synthetic procedure provides an efficient preparation for this useful norlobelane analogue.

AB - An efficient synthesis of cis-2,6-di-(2-quinolylpiperidine) has been developed. The key steps involve Wittig reaction of N-Cbz-protected cis-piperidine-2,6-dicarboxaldehyde (3) with 2-(triphenylphosphinyl-methyl) quinoline bromide (4) and sequential removal of the N-Cbz group and double bond reduction. This synthetic procedure provides an efficient preparation for this useful norlobelane analogue.

KW - Lobelane

KW - Norlobelane analogues

KW - Quinlobelane

KW - Swern oxidation

KW - Wittig reaction

KW - cis-2,6-Di-(2-quinolylpiperidine)

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M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Efficient synthesis of cis-2,6-di-(2-quinolylpiperidine)

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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