File:Quinuclidone synthesis norcamphor.svg

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Summary

Description
Deutsch: Chinuclidon-Synthese ausgehend von Norcampher

Reaktionssequenz:

a: Norcampher (1) reagiert in einer Baeyer-Villiger-Oxidation mit meta-Chloroperoxybenzoesäure zu einem bicyclischen Lacton (2).
b: Es folgt eine Reduktion mit Lithiumaluminiumhydrid in Diethylether zum Diol (3).
c: Die primäre Hydroxylgruppe wird mittels Tosylchlorid und Triethylamin in eine Tosylatgruppe (TsO) in 4 umgewandelt.
d: Anschließend wird diese mit Natriumazid in Dimethylformamid durch eine Azidgruppe substituiert (5).
e: In Dichlormethan wird die verbliebene Hydroxylgruppe durch Dess-Martin-Periodinan zum Keton (6) oxidiert.

f: Den letzte Syntheseschritt stellt eine Schmidt-Reaktion dar, die mit Tetrafluoroborsäure in Diethylether über das Intermediat 7 zum gewünschten Hauptprodukt 2-Chinuclidonium-Tetrafluoroborat (8) und zum Nebenprodukt 9 im Verhältnis 76:24 führt.
English: Quinuclidone synthesis coming from Norcamphor.

Reaction sequence:

First step is a Baeyer-Villiger oxidation of norcamphor 1 with Meta-Chloroperoxybenzoic acid to en:bicyclic lactone 2, followed by organic reduction with lithium aluminium hydride in diethyl ether to diol 3. The primary alcohol group is replaced by a tosylate group in 4 with tosyl chloride and triethylamine and in turn displaced by an azide group in 5 by action of sodium azide in dimethylformamide. Oxidation of the alcohol to the ketone 6 takes place with Dess-Martin periodinane in dichloromethane. The final step to 2-quinuclidonium tetrafluoroborate 8 is a Schmidt reaction through intermediate 7 with fluoroboric acid in diethyl ether. Thereby also the by-product 9 is generated.
Date
Source own work, based on Quinuclidone synthesis norcamphor.png and Clayden, Moran: Das gebogene Amid 2-Chinuclidon: Synthese nach 60 Jahren. Angewandte Chemie 118(43), 2006-11-06, 7276–8
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Date/TimeThumbnailDimensionsUserComment
current14:47, 28 November 2014Thumbnail for version as of 14:47, 28 November 2014700 × 700 (45 KB)Master Ueglytosyl group (ts) replaced by tosylat (TsO)
23:19, 20 February 2012Thumbnail for version as of 23:19, 20 February 2012700 × 700 (40 KB)Master Uegly{{Information |Description ={{de|1=Chinuclidon-Synthese ausgehend von Norcampher Reaktionssequenz:</br> '''a:''' Norcampher ('''1''') reagiert in einer Baeyer-Villiger-Oxidation mit [[:de:meta-Chlorope
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