Synthesis of Tert-butyl 4-formyl-3, 6-dihydropyridine-1(2H) -carboxylate

doi:10.2991/bst-17.2018.41

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Synthesis of Tert-butyl 4-formyl-3, 6-dihydropyridine-1(2H) -carboxylate

Published Feb 1, 2018 · Binliang Zhang, K. Ye, Shan Xu

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Abstract

Tert-butyl 4-formyl-3, 6-dihydropyridine-1(2H)-carboxylate(9) is an important intermediate for small molecule anticancer drugs. A rapid and high yield synthetic method for tert-butyl 4-formyl-3, 6-dihydropyridine-1(2H)-carboxylate was established in this work. The target compound was synthesized from the commercially available piperidin-4-ylmethanol (5) through four steps including nucleophilic substitution reaction, oxidation reaction, halogenation reaction and elimination reaction. The structure of the target product was confirmed by 1 H NMR. In addition, the synthetic method was optimized. The total yield of the four steps was high up to 71.4%. Introduction Dysfunctional signaling of the PI3K/AKT/mTOR pathway in cancer and its crucial role in cell growth and survival had made it a much desired target for cancer therapeutics [1-4]. The use of tyrosine kinas inhibitors has acquired resistance through secondary mutations or by amplification of genes [5-7]. Although a lot of antitumor drugs have been developed, effective drugs that can overcome this resistance problem have not been discovered so far and have not yet reached clinical trials [8-11]. Therefore we need to continue developing and optimizing anti-tumor inhibitors [12-14]. Indeed, there were many small molecule anticancer drugs had been reported in recent years. Among them, many molecules contained the tert-butyl 4-formyl-3, 6-dihydrop yridine-1(2H)-carboxylate(9).The structures of these compounds were shown in Fig.1. For example, 3,5-bis(4-methylbenzoylmethyl)-1-acetyl -4piperidinone(1)[15],methyl 2-(4-benzoyl-1-benzyl-5-ethylpiperidin-3-yl) acetate (2)[16] ,1-methyl-2(3-oxo-3phe nylpropyl)-4-phenylpiperidin-4-yl propionate (3)[17] , 1,3-dibutyl-4(2-methylbenzo yl)-4,6-diphenyl 3,4 –dihydropyridin -2(1H)-one (4) [18].Among them, compound 5 can also be used to develop drugs for the treatment of depression and cerebral ischemia, and compound 3 is a potential analgesic. 263 Copyright © 2018, the Authors. Published by Atlantis Press. This is an open access article under the CC BY-NC license (http://creativecommons.org/licenses/by-nc/4.0/). Advances in Biological Sciences Research (ABSR), volume 6 2017 2nd International Conference on Biological Sciences and Technology (BST 2017)

Study Snapshot

This study developed a rapid and high-yield synthetic method for tert-butyl 4-formyl-3, 6-dihydropyridine-1(2H)-carboxylate, an important intermediate for developing small molecule anticancer drugs.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Synthesis of Tert-butyl 4-formyl-3, 6-dihydropyridine-1(2H) -carboxylate

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