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An improved synthesis of vitamin B6 (pyridoxol)

✍ Scribed by H. M. Wuest; J. A. Bigot; Th. J. de Boer; B. V. D. Wal; J. P. Wibaut

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
973 KB
Volume
78
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The known synthesis of “Ichiba acid”, 2‐methyl‐3‐hydroxypyridine 4,5‐dicarboxylic acid (VII), starting from ethyl acetylpyruvate and cyanoacetamide, has been reinvestigated and simplified to a five step process.

Several derivatives of Ichiba acid have been prepared including the tribenzyl derivative (XIV), with easily accessible dimethylphenylbenzylammonium hydroxide, and the 3‐acetoxy‐anhydride (XVI) with acetic anhydride.

These derivatives are reduced with LiAlH~4~ to vitamin B~6~ (VIII) in yields of 72 and 53% respectively.

Results have been compared with the reduction of related pyridine 4,5‐ dicarboxylic acid derivatives with LiAlH~4~.

📜 SIMILAR VOLUMES

Synthesis of deuterated vitamin B6 compo
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## Abstract 3‐Hydroxy‐4‐(hydroxymethyl)‐5‐(hydroxymethyl‐d~2~)‐2‐methylpyridine(pyridoxine‐d~2~) was prepared by reduction of α^4^‐3‐0‐isopropylidene‐5‐pyridoxic acid with lithium aluminum deuteride. Deuterium was inserted in the 2‐methyl group using base catalyzed exchange between deuterium oxide

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## Abstract Attempts are described to simplify the synthesis of vitamin B~6~ by a simultaneous reduction of the ester groups and reductive elimination of the chlorine atom in dimethyl 3‐amino‐6‐chloro‐2‐methylpyridine‐4,5‐dicarboxylate (III) with lithium aluminium hydride. After prolonged refluxing