cas 702-82-9, 3-Amino-1-hydroxyadamantane | Articles data

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A facile method to synthesize vildagliptin
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%.
Zhang, Li,Jiang, Lan,Guan, Xiaoshu,Cai, Linhong,Wang, Jingyu,Xiang, Peng,Pan, Junyi,Hu, Xiangnan
p. 305 - 309
(2020/12/01)

3 - Amino -1 - adamantanol and preparation method and application thereof
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.
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Paragraph 0028; 0030-0045

(2021/10/02)

3-(dimethylaminomethyl) piperidine-4-alcohol derivative as well as preparation method and pharmaceutical application thereof
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.
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Paragraph 0206-0210

(2021/05/08)

3-amino-1-adamantanol and synthesis method thereof
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.
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Paragraph 0050-0078; 0084-0085

(2021/04/26)

Ozone-Mediated Amine Oxidation and Beyond: A Solvent-Free, Flow-Chemistry Approach
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.
Skrotzki, Eric A.,Vandavasi, Jaya Kishore,Newman, Stephen G.
p. 14169 - 14176
(2021/06/30)

Cerium-Catalyzed C-H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents
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.
An, Qing,Chen, Yuegang,Liu, Weimin,Pan, Hui,Wang, Xin,Wang, Ziyu,Zhang, Kaining,Zuo, Zhiwei
p. 6216 - 6226
(2020/04/27)

Method for preparing 3- amino -1- adamantane alcohol
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.
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Paragraph 0042; 0045-0049; 0052-0053; 0056-0057; 0060-0061

(2020/04/29)

Synthesis method of 3-amino-1-adamantanol
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.
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Paragraph 0016-0018

(2020/06/16)

Process for preparing 3-amino-1-adamantanol
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.
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Paragraph 0018-0022

(2019/07/04)

Synthesis and identifications of potential metabolites as biomarkers of the synthetic cannabinoid AKB-48
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.
Wallgren, Jakob,Vikingsson, Svante,?strand, Anna,Josefsson, Martin,Gréen, Henrik,Dahlén, Johan,Wu, Xiongyu,Konradsson, Peter
p. 2905 - 2913
(2018/05/16)

Synthesis and identification of an important metabolite of AKB-48 with a secondary hydroxyl group on the adamantyl ring
Studies on the metabolism of bioactive substances containing the adamantyl moiety have shown that hydroxylation is likely to occur at a tertiary carbon of adamantane. Herein, we report the synthesis and identification of one major metabolite of AKB-48, a new illicit psychoactive substance with a hydroxyl group at a secondary carbon of the adamantyl ring.
Wallgren, Jakob,Vikingsson, Svante,Johansson, Anders,Josefsson, Martin,Green, Henrik,Dahlén, Johan,Wu, Xiongyu,Konradsson, Peter
supporting information
p. 1456 - 1458
(2017/03/23)

Compound with potential therapeutic activity on diabetes
The invention relates to a compound with the potential therapeutic activity on diabetes. The compound has a general formula (please see the formula in the description), wherein X can be groups such as hydrogen, an alkyl group, halogen, a hydroxyl group, a hydrocarbon oxygen group, an acyloxy group, an aldehyde group, an acyl group, a nitro group, an amino group, a hydrocarbon ammonia group, a carboxy group, an acyl halide group, an acyl-oxygen acyl group, an ester group, an acylamino group, a cyano group, a guanidine group, an amidine group, an azide group and an inorganic acid ester group, n is larger than or equal to 0, Y can be heteroatom or 1,2-vinylidene or methylene or free of atoms; Z can be substituted at the 2 position, the 3 position and the 4 position of an adamantane ring and can be common organic groups such as hydrogen, an alkyl group, halogen, a hydroxyl group, a hydrocarbon oxygen group, an acyloxy group, an aldehyde group, an acyl group, a nitro group, an amino group, a hydrocarbon ammonia group, a carboxy group, an acyl halide group, an acyl-oxygen acyl group, an ester group, an acylamino group and a cyano group.
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Paragraph 0033; 0034; 0035

(2017/04/03)

A process for preparing VIDA row sandbank key intermediate 3 - amino - 1 - adamantane method
The invention relates to a method for preparing key intermediate 3-amino-1-adamantanol of vildagliptin. The 3-amino-1-adamantanol is prepared by taking low-price amantadine hydrochloride as an initial raw material and adopting a mixed acid method in which different acids are changed. The method is mainly characterized in that the rate of charge of fuming sulphuric acid, trifluoroacetic acid, nitric acid and amantadine hydrochloride in reaction and temperature and time in the reaction process are controlled, so that the yield of the product is greatly improved. In addition, the method provided by the invention further has the advantages of available raw material, low price, mild reaction condition, short time, less environmental pollution, cost reduction due to recycled solvent and the like, and is simple to operate and suitable for industrialized production.
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Paragraph 0020; 0021; 0022

(2017/10/20)

One-pot synthesis of cage alcohols
An efficient one-pot procedure has been developed for the synthesis of cage alcohols with hydroxy groups in the bridgehead positions. The procedure includes initial nitroxylation with nitric acid or a mixture of nitric acid with acetic acid and subsequent hydrolysis in the presence of urea.
Klimochkin, Yu. N.,Yudashkin,Zhilkina,Ivleva,Moiseev,Oshis, Ya. F.
p. 971 - 976
(2017/09/07)

Discovery of Novel Adenosine Receptor Agonists That Exhibit Subtype Selectivity
A series of N6-bicyclic and N6-(2-hydroxy)cyclopentyl derivatives of adenosine were synthesized as novel A1R agonists and their A1R/A2R selectivity assessed using a simple yeast screening platform. We observed that the most selective, high potency ligands were achieved through N6-adamantyl substitution in combination with 5′-N-ethylcarboxamido or 5′-hydroxymethyl groups. In addition, we determined that 5′-(2-fluoro)thiophenyl derivatives all failed to generate a signaling response despite showing an interaction with the A1R. Some selected compounds were also tested on A1R and A3R in mammalian cells revealing that four of them are entirely A1R-selective agonists. By using in silico homology modeling and ligand docking, we provide insight into their mechanisms of recognition and activation of the A1R. We believe that given the broad tissue distribution, but contrasting signaling profiles, of adenosine receptor subtypes, these compounds might have therapeutic potential.
Knight, Anthony,Hemmings, Jennifer L.,Winfield, Ian,Leuenberger, Michele,Frattini, Eugenia,Frenguelli, Bruno G.,Dowell, Simon J.,Lochner, Martin,Ladds, Graham
supporting information
p. 947 - 964
(2016/02/23)

4-oxo-1,4-dihydroquinoline-3-carboxamide as selective ligand for cannabinoid receptor 2 for diagnosis and therapy
The present invention is directed to new compounds selectively binding the cannabinoid 2 receptor. In addition, the invention relates to the use of said compounds for determining cannabinoid receptor 2 (CB2)-selective receptor localization and density, preferably in the central nervous system (CNS), the peripheral nervous system (PNS), heart, liver, gastrointestinal tract, spleen, pancreas, kidney, testis, ovary and/or the prostate. Moreover, the invention pertains to the use of said compounds in the diagnosis, prophylaxis and/or therapy of CB2 receptor-related diseases.
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Paragraph 0063; 0069

(2016/03/18)

Preparation method of vildagliptin
The invention discloses a preparation method of vildagliptin; a non-homogeneous system with acetonitrile as a main solvent and potassium carbonate and iodine salt as main components is used, two key fragments of (S)-1-(2-chloroacetyl chloride)-2-nitrile pyrrolidine and 3-amino-1-adamantanol are coupled to prepare vildagliptin, and the intermediate conversion rate and the yield are both superior to those of the prior art; the preparation method adopts iodine ion salt for activating chlorine in a reactant structure, and a phase transfer catalyst is selected to be added for promoting the effect of a non-homogeneous reaction.
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Paragraph 0049; 0050; 0051; 0052; 0053

(2017/02/09)

Improved device for production of 3-amino-1-adamantanol
The invention belongs to the field of chemical production, and in particular relates to an improved device for production of 3-amino-1-adamantanol. The improved device for the production of 3-amino-1-adamantanol comprises a reaction liquid storage tank, a magnetic pump and a reaction kettle with stirring paddles which are connected in sequence through a liquid guiding pipe; an ultrasound device is arranged between the reaction liquid storage tank and the magnetic pump; the ultrasonic device comprises a box body, an ultrasonic vibration plate arranged inside the box body and an ultrasonic generator connected with the ultrasonic vibration plate and arranged outside the box body; the inlet end of the box body is connected with the bottom of the reaction liquid storage tank, and the outlet end of the box body is connected with the magnetic pump. According to the invention, the ultrasonic vibration plate of the ultrasound device is used for vibrating and shattering bubbles and then a reaction liquid flows into the magnetic pump, and is pumped into the top of the reaction kettle by the magnetic pump, so that the phenomenon of the bubble-inclusion liquid can be greatly reduced; the single impurity content of the finished 3-amino-1-adamantanol is lowered below 0.3%, so that the content of the product is increased.
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Paragraph 0022-0024

(2018/02/04)

3-hydroxy-1-amantadine preparation method
The present invention discloses a 3-hydroxy-1-amantadine (2) preparation method. The target product (2) is an important intermediate of new drug vildagliptin for the treatment of hyperlipidemia. According to the method, an organic base alcohol solution is used for neutralizing excess mixed acid during nitrification, and is used as a catalyst for hydrolysis reaction, so that the product and inorganic salts are easy to separate, and the defects that due to the difficulty of inorganic salt and product separation in the prior art, an aqueous solution needs distillation and concentration, then a large number of dichloromethane is used for extraction and separation, yield is low, cost is high and the environment and human health are impacted can be overcome. The new method is simple, high in yield and good in purity of the product, does not affect the environment and human health, and is in favor of industrial scale production.
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Paragraph 009; 0019; 0020

(2016/10/08)

Synthesis, radiolabeling and evaluation of novel 4-oxo-quinoline derivatives as PET tracers for imaging cannabinoid type 2 receptor
Our goal is to develop a highly specific and selective PET brain tracer for imaging CB2 expression in patients with neuroinflammatory diseases. Based on our previous findings on a carbon-11 labeled 4-oxoquinoline structure, designated KD2, further structural optimizations were performed, which led to the discovery of N-(1-adamantyl)-1-(2-ethoxyethyl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide (RS-016). Compared to KD2, RS-016 exhibits a higher binding affinity towards CB2 (Ki = 0.7 nM) with a selectivity over CB1 of >10,000 and lower lipophilicity (logD7.4 = 2.78). [11C]RS-016 was obtained in 99% radiochemical purity and up to 850 GBq/mmol specific radioactivity at the end of synthesis. In vitro autoradiography on rodent spleen tissue showed high specific binding to CB2. [11C]RS-016 was stable in vitro in rodent and human plasma over 40 min, whereas 47% intact compound was found in vivo in rat blood plasma 20 min post injection (p.i.). High specific binding to CB2 was observed in murine spleen tissues and postmortem ALS patient spinal cord tissues in vitro autoradiography, ex vivo biodistribution data confirmed the high and specific uptake of [11C]RS-016 in spleen region in rats. In vivo specificity of [11C]RS-016 could also be shown in brain by PET imaging using a murine neuroinflammation model, which has higher CB2 receptor expression level in the brain induced by lipopolysaccharide (LPS) application.
Slavik, Roger,Herde, Adrienne Müller,Bieri, Daniel,Weber, Markus,Schibli, Roger,Kr?mer, Stefanie D.,Ametamey, Simon M.,Mu, Linjing
p. 554 - 564
(2015/01/30)

NOVEL ECONOMIC PROCESS FOR VILDAGLIPTIN
The present invention relates to a commercially viable novel process for manufacturing Vildagliptin in high yield with high chemical and chiral purity.
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Page/Page column 15

(2015/09/28)

PROCESS FOR PREPARATION OF DPP-IV INHIBITORS
Process for the preparation of DPP-IV inhibitors, such as 1-[[(3-hydroxy-1-adamantyl) amino] acetyl]-2-cyano-(S)-pyrrolidine are disclosed.
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Page/Page column 17

(2011/09/19)

Selective hydroxylation of adamantane and its derivatives
A general method was developed for hydroxylation into the nodal position of adamantane and its 1- and 2-substituted derivatives employing systems H 2O-CBr4 (BrCCl3, CCl4) in the presence of complexes of Pd, Ni, Ru, Co, Mo, W, and Fe. The oxidants in the systems are hypochlorous (HOCl) or hypobromous (HOBr) acids generated from water and halomethanes under the reaction conditions.
Khusnutdinov,Shchadneva,Mukhametshina,Dzhemilev
scheme or table
p. 1137 - 1142
(2009/12/03)

N-(substituted glycyl)-2-cyanopyrrolidines, pharmaceutical compositions containing them and their use in inhibiting dipeptidyl peptidase-IV
The present invention relates to a compound of formula (I) wherein R is substituted adamantyl; and n is 0 to 3; in free form or in acid addition salt form. Compounds of formula I inhibit DPP-IV (dipeptidyl-peptidase-IV) activity. They are therefore indicated for use as pharmaceuticals in inhibiting DPP-IV and in the treatment of conditions mediated by DPP-IV, such as non-insulin-dependent diabetes mellitus, arthritis, obesity, osteoporosis and further conditions of impaired glucose tolerance.
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(2008/06/13)

POLYMERIZABLE ADAMANTANE DERIVATIVES AND PROCESS FOR PRODUCING THE SAME
A compound shown by the following formula: ???wherein each of R1a, R2a, R3aand R4arepresents a substituent selected from a non-reactive atom, a non-reactive group, a hydroxyl group and an amino group, and at least two members selected from R1a, R2a, R3aand R4aare a hydroxyl group, a carboxyl group or an amino group; is subjected to an esterification reaction or an amidation reaction with a polymerizable unsaturated compound (e.g., an alcohol, a carboxylic acid, an amine) in the presence of a catalyst comprising an element selected from the Group 3 elements, such as a samarium compound, to obtain a polymerizable adamantane derivative having at least one polymerizable unsaturated group in high yield.
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(2008/06/13)

AMINO BI- AND TRI-CARBOCYCLIC AKLANE BIS-ARYL SQUALENE SYNTHASE INHIBITORS
This invention relates to a class of novel amino bi- and tri-carbocyclic alkane compounds having bis-aryl substitution which exhibit squalene synthase inhibition properties. The bi- and tri-carbocyclic alkane ring contains an amino group and the ring is further linked or bridged to two mono- and/or bicyclic rings. Compounds of this invention reduce levels of serum cholesterol in the body without significantly reducing mevalonic metabolite synthesis. This invention relates also to pharmacological compositions and method of treatment for lowering serum cholesterol levels using the compounds of this invention.
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(2008/06/13)

Regioselective oxyfunctionalization of unactivated tertiary and secondary C-H bonds of alkylamines by methyl(trifluoromethyl)dioxirane in acid medium
Tetrafluoroborate salts of primary, secondary, and tertiary alkylamines are resistant toward N oxidation by methyl(trifluoromethyl)dioxirane (1b), which allows the selective oxidation of aliphatic tertiary and secondary C-H bonds in the alkyl side chain. The oxidations are carried out at 0°C with a ketone-free solution of methyl(trifluoromethyl)-dioxirane (1b) in methylene chloride. By this procedure, within 3 h the tertiary C-H bonds of acyclic, cyclic, and polycyclic amines 2a-e are hydroxylated to give the corresponding amino alcohols 3a-e. In the case of the acyclic amines 2a,b longer reaction times were necessary, and in the strong acid medium the corresponding amino acetamides 4a,b were obtained through Ritter reaction with the solvent acetonitrile. The strong electron-withdrawing nature of the ammonium group deactivates the oxidation of even tertiary C-H bonds at the α and β positions. Secondary C-H bonds of the linear aliphatic primary amines 2f-h were oxidized exclusively at the ∈ position to give the 2,3,4,5-tetrahydro-6-alkylpyridines 6f-h after intramolecular condensation of the corresponding amino ketones 5f-h.
Asensio, Gregorio,González-Nú?ez, María Elena,Bernardini, Carmen Boix,Mello, Rossella,Adam, Waldemar
p. 7250 - 7253
(2007/10/02)

SYNTHESIS AND BIOLOGICAL ACTIVITY OF SOME 1-HYDROXY-3-AMINOALKYLADAMANTANES AND THEIR DERIVATIVES
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Lavrova, L. N.,Indulen, M. K.,Ryazantseva, G. M.,Korytnyi, V. S.,Yashunskii, V. G.
p. 35 - 39
(2007/10/02)