Tetrahedron

The synthesis of novel GABA uptake inhibitors. Part 2. Synthesis of 5-hydroxytiagabine, a human metabolite of the GABA reuptake inhibitor tiagabine

KE Andersen, M Begtrup, MS Chorghade, EC Lee…

文献索引：Andersen, Knud E.; Begtrup, Mikael; Chorghade, Mukund S.; Lee, Elaine C.; Lau, Jesper; et al. Tetrahedron, 1994 , vol. 50, # 29 p. 8699 - 8710

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被引用次数: 17

摘要

(R)-1-(4-(2, 5-Dihydro-3-methyl-5-oxothien-2-ylidene)-4-(3-methyl-2-thienyl) butyl)-3- piperidinecarboxylic acid (5-hydroxytiagabine) 13, has been prepared in 8 steps from 2- bromo-3-methylthiophene 3. Key steps are Grignard reactions, displacement of heteroaromatic chlorine with methoxy, and simultaneously demethylation and opening of a hydroxymethylcyclopropane with bromotrimethylsilane. An alternative approach involving ...