702-82-9Relevant articles and documents
3-(dimethylaminomethyl) piperidine-4-alcohol derivative as well as preparation method and pharmaceutical application thereof
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Paragraph 0206-0210, (2021/05/08)
The present invention provides compounds of formula (FWBF) or pharmaceutically acceptable salts thereof, in which the substituents are as defined in the specification, as well as a preparation method and pharmaceutical use thereof.
Ozone-Mediated Amine Oxidation and Beyond: A Solvent-Free, Flow-Chemistry Approach
Skrotzki, Eric A.,Vandavasi, Jaya Kishore,Newman, Stephen G.
, p. 14169 - 14176 (2021/06/30)
Ozone is a powerful oxidant, most commonly used for oxidation of alkenes to carbonyls. The synthetic utility of other ozone-mediated reactions is hindered by its high reactivity and propensity to overoxidize organic molecules, including most solvents. This challenge can largely be mitigated by adsorbing both substrate and ozone onto silica gel, providing a solvent-free oxidation method. In this manuscript, a flow-based packed bed reactor approach is described that provides exceptional control of reaction temperature and time to achieve improved control and chemoselectivity over this challenging transformation. A powerful method to oxidize primary amines into nitroalkanes is achieved. Examples of pyridine, C-H bond, and arene oxidations are also demonstrated, confirming the system is generalizable to diverse ozone-mediated processes.
A facile method to synthesize vildagliptin
Zhang, Li,Jiang, Lan,Guan, Xiaoshu,Cai, Linhong,Wang, Jingyu,Xiang, Peng,Pan, Junyi,Hu, Xiangnan
, p. 305 - 309 (2020/12/01)
An efficient and high-yielding synthetic method for the preparation of vildagliptin via four steps is reported. The process starts from L-proline and involves a successful reaction with chloroacetyl chloride in tetrahydrofuran to afford (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid, followed by a reaction with acetonitrile in the presence of sulfuric acid to give (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile. This is then reacted with 3-aminoadamantanol to give vildagliptin. 3-Aminoadamantanol is prepared from 1-aminoadamantane hydrochloride via oxidation with sulfuric acid/nitric acid and boric acid as the catalyst followed by ethanol extraction. The overall yield is 95%.
3 - Amino -1 - adamantanol and preparation method and application thereof
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Paragraph 0028; 0030-0045, (2021/10/02)
The invention relates to the technical field of chemical synthesis preparation, in particular to 3 - amino -1 - adamantanol and a preparation method and application thereof. The method comprises the following steps. After a period of time, crushed ice is added, and then crushed ice is added until the reaction solution becomes clear ink green, pH values are adjusted to obtain the product, and the product is refluxed and filtered through the organic solution A and the organic solution B, respectively. After drying, 3 - amino -1 - adamantane is obtained. The 3 - amino -1 - adamantanol with high yield can be obtained through cheap and easily available raw materials and simple operation, and the method is low in cost, fast in reaction and more suitable for industrial production.
3-amino-1-adamantanol and synthesis method thereof
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Paragraph 0050-0078; 0084-0085, (2021/04/26)
The invention relates to the technical field of organic synthesis, in particular to 3-amino-1-adamantanol and a synthesis method thereof. The synthesis method of 3-amino-1-adamantanol comprises the following steps of: mixing 3-acetyl amino-1-adamantanol, strong base and an alcohol solvent, heating to 100-200 DEG C in a closed environment, reacting for 5-10h, cooling, crystallizing, filtering, washing the filter cake with the alcohol solvent, merging the filtrate, and distilling to remove the solvent, thereby obtaining the 3-amino-1-adamantanol. The synthesis method of 3-amino-1-adamantanol provided by the invention has the characteristics of simple steps, easiness in operation, high yield, high efficiency and suitability for industrial production; and the used raw material is adamantane, and special adamantane derivatives such as amantadine and adamantanecarboxylic acid are not needed as raw materials, so that the production cost is further reduced.
Synthesis method of 3-amino-1-adamantanol
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Paragraph 0016-0018, (2020/06/16)
The invention discloses a synthesis method of 3-amino-1-adamantanol. Adamantanecarboxylic acid is used as a substrate, and the preparation method comprises the following steps of: (1) slowly adding adamantanecarboxylic acid into liquid bromine, and synthesizing 3-bromine-1-adamantanecarboxylic acid under the action of an anhydrous aluminum trichloride catalyst, (2) reacting the synthesized 3-bromine-1-adamantanecarboxylic acid with triethylamine, diphenyl azide phosphate and tert-butyl alcohol in an organic solvent at the temperature of 80-110 DEG C for 12-16 hours to synthesize 3-bromine-1-tert-butoxycarbonylamidated adamantine, (3) carrying out reflux reaction on the 3-bromine-1-tert-butoxycarbonylamidated adamantine in an excessive amount of hydrobromic acid solution with the molar concentration of 10% for 24-48 hours, and (4) adding the synthesized bromate type 3-amino-1-adamantanol into an equimolar sodium hydroxide solution, heating to 30 DEG C while stirring, cooling to separateout a solid, carrying out suction filtration, and carrying out vacuum drying to obtain the 3-amino-1-adamantanol. The method is simple in steps, easy to operate, environment-friendly, low in cost andhigh in yield, and has the characteristic of suitability for industrial production.
Cerium-Catalyzed C-H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents
An, Qing,Chen, Yuegang,Liu, Weimin,Pan, Hui,Wang, Xin,Wang, Ziyu,Zhang, Kaining,Zuo, Zhiwei
, p. 6216 - 6226 (2020/04/27)
Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization of light energy for the activation of organic substrates. Here, we demonstrate the catalytic application of ligand-to-metal charge-transfer (LMCT) excitation of cerium alkoxide complexes for the facile activation of alkanes utilizing abundant and inexpensive cerium trichloride as the catalyst. As demonstrated by cerium-catalyzed C-H amination and the alkylation of hydrocarbons, this reaction manifold has enabled the facile use of abundant alcohols as practical and selective hydrogen atom transfer (HAT) agents via the direct access of energetically challenging alkoxy radicals. Furthermore, the LMCT excitation event has been investigated through a series of spectroscopic experiments, revealing a rapid bond homolysis process and an effective production of alkoxy radicals, collectively ruling out the LMCT/homolysis event as the rate-determining step of this C-H functionalization.
Method for preparing 3- amino -1- adamantane alcohol
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Paragraph 0042; 0045-0049; 0052-0053; 0056-0057; 0060-0061, (2020/04/29)
The invention discloses a preparation method of 3-amino-1-adamantanol, which comprises following steps: (1) adding amantadine or a salt thereof to sulfuric acid at 10-30 DEG C and adding dropwisely a mixed acid to perform a nitration reaction to obtain a reaction liquid; (2) adding the reaction liquid to water and mixing the reaction liquid with water to obtain a mixed solution; (3) performing a hydroxylation reaction under the effect of an alkaline to obtain the 3-amino-1-adamantanol . The preparation method employs the raw material being easy to obtain, is simple in operations, is environmental-protective, is low in cost, is high in yield which is generally higher than 80%, maximally 90.1%, and is more suitable for industrial production.
Process for preparing 3-amino-1-adamantanol
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Paragraph 0018-0022, (2019/07/04)
The invention discloses a process for preparing 3-amino-1-adamantanol. An amantadine sulphuric acid solution and a nitric acid solution are respectively injected into a microchannel reactor for a stayreaction at 45-90 DEG C, cooling is conducted after the reaction is finished, reaction liquid is injected into ice water to quench, alkali is added to adjust the pH to be 12-14, hydrolysis is conducted at 50-90 DEG C to obtain a solid, and centrifugation is conducted to obtain the solid 3-amino-1-adamantanol. By means of the preparation process, the phenomenon that heat release of a nitration reaction is violent is avoided, and the risk of production is lowered; meanwhile, the phenomenon that due to partial overheating, nitric acid decomposition is caused is avoided, consumption of raw materials is reduced, pollution is reduced, and meanwhile production of a by-product dinitro is reduced, and the molar yield of the product is increased. By means of the process, continuous, efficient, safeand energy-saving industrial production can be achieved, the preparation process is simple, the reaction is controllable, the stay time is short, the product quality is stable, acid consumption is reduced, the number of three wastes is greatly reduced, and the process is very beneficial to industrial promotion and application.
Synthesis and identifications of potential metabolites as biomarkers of the synthetic cannabinoid AKB-48
Wallgren, Jakob,Vikingsson, Svante,?strand, Anna,Josefsson, Martin,Gréen, Henrik,Dahlén, Johan,Wu, Xiongyu,Konradsson, Peter
, p. 2905 - 2913 (2018/05/16)
AKB-48 belongs to the family of synthetic cannabinoids. It has strong binding affinity to CB1 receptor and is psychoactive. It is banned in many countries including USA, Japan, Germany, New Zealand, Singapore and China etc. But the difficulty in detecting the parent compound in urine samples highlights the importance of studies of its metabolites. Here we report the synthesis of 19 potential metabolites of AKB-48, among which, compounds 2, 9, 10, 30 and 31, together with the commercially available substance 5 were identified as metabolites of AKB-48 by comparison with one authentic human urine sample and human liver microsomal data. Compounds 10 and 30 could be of use as biomarkers in detecting AKB-48 in human urine samples.
