Synthesis of 4-(pyrrolidin-1-ylmethyl)benzaldehyde

doi:10.2991/bst-17.2018.37

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Synthesis of 4-(pyrrolidin-1-ylmethyl)benzaldehyde

Published Feb 1, 2018 · Binliang Zhang, Lu-Jie Cao, Shan Xu

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Abstract

4-(pyrrolidin-1-ylmethyl)benzaldehyde (1) as a water-soluble aldehyde is an important intermediate for small molecule anticancer drugs. A rapid and high yield synthetic method for 4-(pyrrolidin-1-ylmethyl)benzaldehyde (1) was established in this work. The target compound was synthesized from the commercially available terephthalaldehyde (6) through three steps including acetal reaction, nucleophilic reaction and hydrolysis reaction. The structure of the target product was confirmed by 1 H NMR and MS. In addition, the synthetic method was optimized. The total yield of the three steps was high up to 68.9%. Introduction Cancer is a serious disease that threatens human health and life. More than 100 types of cancer are currently known [1-4]. Most cancers are named after the organ that originally produced the cancer cells, such as rectal cancer, lung cancer and the like[5-6].And also named by the cell type of the cancer cells, for example, cancer cells located on the basal layer of the skin are called basal cell carcinomas carcinoma[7-10]. Cancer is one of biggest killer of human beings, taking the lives of over 7 million people a year. With the further understanding of human signaling pathways, many signaling pathways are found to be closely related to tumors such as EGFR, c-Met and other pathways [11-12]. Through deep research on these pathways, many anti-tumor drugs have been developed, but the drug resistance and adverse side effects are still serious problems [13-14]. Therefore, it is still necessary to continue to develop new antitumor drugs and improve the selectivity, efficiency and safety of anticancer drugs. In recent years, there were many small molecule anticancer drugs had been reported. Among them, many molecules contained the 4-(pyrrolidin-1-ylmeth yl)benzaldehyde. Therefore, design and synthesis of 4-(pyrrolidin-1-ylmethyl) benzaldehyde derivative as small molecule inhibitors played a great role in the study of anticancer drugs. The structures of these compounds were shown in Fig.1. For example, 4-(((3S,4S)-3, 4-bis(benzyloxy)pyrrolidin-1-yl)methyl)benzaldehyde(2)[15], methyl 2-acetyl-4((2-methyl-5-oxo-3-(p-tolyl)pyrrolidin-1-yl)methyl) benzoate (3) [16] , 1-(4-acetyl-2(4-chloro-3-fluorophenoxy)benzyl)pyrrolidin-2-one(4),ethyl 1(3-acetyl-4(meth -oxycarbonyl)benzyl)-5-methyl-2-oxo-4-(p-tolyl)pyrrolidine-3-carboxylate(5)[17]. At the same time, compound 5 is a potential receptor antagonist with a great potential for research and development, while compound 6 is a potential anti-inflammatory The synthesis of most 4-(pyrrolidin-1-ylmethyl)benzaldehyde (1) is reported. In the literature, there are shortcomings in the synthesis route, such as by-products more, long reaction time. 4-(pyrrolidin-1-ylmethyl)benzaldehyde (1) is a key intermediate for anti breast cancer, lymphoma and colon cancer. Therefore, In this study, we designed and optimized the synthesis of 4-(pyrrolidin-1-ylmethyl)benzaldehydee (1), 247 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)

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This study developed a rapid and high-yield synthetic method for 4-(pyrrolidin-1-ylmethyl)benzaldehyde, an important intermediate for small molecule anticancer drugs, with a total yield of up to 68.9%.

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 4-(pyrrolidin-1-ylmethyl)benzaldehyde

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