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Synthesis of deuterium labelled thioridazine via ruthenium tetroxide oxidation of the piperidine ring

โœ Scribed by T. Mohammad; K. K. Midha; E. M. Hawes

Publisher
John Wiley and Sons
Year
1988
Tongue
French
Weight
609 KB
Volume
25
Category
Article
ISSN
0022-2135

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โœฆ Synopsis

A multistep synthetic route to (~)-10-[2-(1-methyl-2-piperidinyl)ethyl]-2-methylthio-lOH-phenothiazine (thioridazine) was developed which allowed for the incorporation of two deuterium atoms in the piperidine ring and a further two in the 1-position of the ethyl side chain. The key steps involved ruthenium tetroxide oxidation of N-protected methyl 2-piperidinylacetate and subsequent lifhium aluminum deuteride reduction of 2-(2-hydroxyethyl)-l-methyl-6-piperidinone or the corresponding piperidinoneester. The isotopic plrity of the dideuterated and tetradeuterated products was greater than 99%.

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An improved synthesis of dideuterated th
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