Synthesis of the 2β,3β-, 2α,3β-, 2β,3α- and 2α,3α-isomers of 6β-hydroxy-3-(p-tolyl)tropane-2-carboxylic acid methyl ester

Lianyun Zhao; Alan P. Kozikowski

doi:10.1016/S0040-4039(99)00869-2

Synthesis of the 2β,3β-, 2α,3β-, 2β,3α- and 2α,3α-isomers of 6β-hydroxy-3-(p-tolyl)tropane-2-carboxylic acid methyl ester

Lianyun Zhao, Alan P. Kozikowski

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

9 Scopus citations

Abstract

6-Hydroxytropanone (8) was synthesized by a Mannich type condensation between acetonedicarboxylic acid, methylamine hydrochloride, and the hydrolysis product of 2,5-dimethoxydihydrofuran and was used as the key intermediate for the synthesis of the four racemic isomers of 6β-hydroxy-2- (methoxycarbonyl)-3-(p-tolyl)tropane.

Original language	English (US)
Pages (from-to)	4961-4964
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	27
DOIs	https://doi.org/10.1016/S0040-4039(99)00869-2
State	Published - Jul 2 1999
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis of the 2β,3β-, 2α,3β-, 2β,3α- and 2α,3α-isomers of 6β-hydroxy-3-(p-tolyl)tropane-2-carboxylic acid methyl ester",

abstract = "6-Hydroxytropanone (8) was synthesized by a Mannich type condensation between acetonedicarboxylic acid, methylamine hydrochloride, and the hydrolysis product of 2,5-dimethoxydihydrofuran and was used as the key intermediate for the synthesis of the four racemic isomers of 6β-hydroxy-2- (methoxycarbonyl)-3-(p-tolyl)tropane.",

author = "Lianyun Zhao and Kozikowski, {Alan P.}",

year = "1999",

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doi = "10.1016/S0040-4039(99)00869-2",

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T1 - Synthesis of the 2β,3β-, 2α,3β-, 2β,3α- and 2α,3α-isomers of 6β-hydroxy-3-(p-tolyl)tropane-2-carboxylic acid methyl ester

AU - Zhao, Lianyun

AU - Kozikowski, Alan P.

PY - 1999/7/2

Y1 - 1999/7/2

N2 - 6-Hydroxytropanone (8) was synthesized by a Mannich type condensation between acetonedicarboxylic acid, methylamine hydrochloride, and the hydrolysis product of 2,5-dimethoxydihydrofuran and was used as the key intermediate for the synthesis of the four racemic isomers of 6β-hydroxy-2- (methoxycarbonyl)-3-(p-tolyl)tropane.

AB - 6-Hydroxytropanone (8) was synthesized by a Mannich type condensation between acetonedicarboxylic acid, methylamine hydrochloride, and the hydrolysis product of 2,5-dimethoxydihydrofuran and was used as the key intermediate for the synthesis of the four racemic isomers of 6β-hydroxy-2- (methoxycarbonyl)-3-(p-tolyl)tropane.

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U2 - 10.1016/S0040-4039(99)00869-2

DO - 10.1016/S0040-4039(99)00869-2

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Synthesis of the 2β,3β-, 2α,3β-, 2β,3α- and 2α,3α-isomers of 6β-hydroxy-3-(p-tolyl)tropane-2-carboxylic acid methyl ester

Abstract

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