68579-60-2Relevant articles and documents
5-Aryloxazolidines as Reagents for Double Alkylation of Arenes: A Novel Synthesis of 4-Aryltetrahydroisoquinolines
Buev, Evgeny M.,Moshkin, Vladimir S.,Smorodina, Anastasia A.,Sosnovskikh, Vyacheslav Y.
, p. 15307 - 15317 (2021/10/20)
5-Aryloxazolidines react with arenes under Lewis or Br?nsted acid conditions via the Friedel-Crafts/Pictet-Spengler double alkylation sequence to give alkaloid-like 4-aryltetrahydroisoquinolines in 12-94% yields. Three approaches for the controlled insertion of substituents into the target molecules and application of oxazolidine derivatives such as 1-arylethanol-2-amines or 4-hydroxytetrahydroisoquinolines in the alkylation of arenes are also described. An unprecedented two-step easily scalable synthesis of the 4-aryltetrahydroisoquinoline core from aromatic aldehyde was achieved applying oxazolidine methodology.
Catalyst-Free Visible-Light-Mediated Iodoamination of Olefins and Synthetic Applications
Engl, Sebastian,Reiser, Oliver
supporting information, p. 5581 - 5586 (2021/07/26)
Herein we report a catalyst- and metal-free visible-light-mediated protocol enabling the iodoamination of miscellaneous olefins. This protocol is characterized by high yields under environmentally benign reaction conditions utilizing commercially available substrates and a green and biodegradable solvent. Furthermore, the protocol allows for late-stage functionalization of bioactive molecules and can be scaled to gram quantities of product, which offers manifold possibilities for further transformations, including morpholine, piperidine, pyrrolidine, and aziridine synthesis.
Design and Scalable Synthesis of N-Alkylhydroxylamine Reagents for the Direct Iron-Catalyzed Installation of Medicinally Relevant Amines**
Delcaillau, Tristan,Falk, Eric,Gürtler, Laura,Makai, Szabolcs,Morandi, Bill
supporting information, p. 21064 - 21071 (2020/09/21)
Secondary and tertiary alkylamines are privileged substance classes that are often found in pharmaceuticals and other biologically active small molecules. Herein, we report their direct synthesis from alkenes through an aminative difunctionalization reaction enabled by iron catalysis. A family of ten novel hydroxylamine-derived aminating reagents were designed for the installation of several medicinally relevant amine groups, such as methylamine, morpholine and piperazine, through the aminochlorination of alkenes. The method has excellent functional group tolerance and a broad scope of alkenes was converted to the corresponding products, including several drug-like molecules. Besides aminochlorination, the installation of other functionalities through aminoazidation, aminohydroxylation and even intramolecular carboamination reactions, was demonstrated, further highlighting the broad potential of these new reagents for the discovery of novel amination reactions.
Method for synthesizing N-methylphenethyl ethanolamine and hydrochloride thereof
-
Paragraph 0039; 0045-0058, (2017/08/30)
The invention relates to a method for synthesizing N-methylphenethyl ethanolamine and hydrochloride thereof, and belongs to the technical field of organic synthesis. The method comprises the following steps: dissolving styrene and sodium chloride in a mixed solvent, sequentially adding sulfuric acid aqueous solution and sodium periodate at negative 5-5 DEG C, heating and stirring to react, adding a sodium thiosulfate aqueous solution for a quenching reaction, regulating the pH value to be 8, extracting and concentrating to obtain intermediate (I); adding a methylamine aqueous solution into a reaction bottle, slowly dropwise adding the intermediate (I) into the reaction bottle, stirring overnight at room temperature, performing HPLC detection reaction, and concentrating at reduced pressure to obtain the N-methylphenethyl ethanolamine. In the method for synthesizing N-methylphenethyl ethanolamine, raw materials have low price and are easily available, a low-price conventional reagent is adopted as the reagent, so that the method has low synthesizing cost, mild reaction condition and high conversion rate; and the prepared N-methylphenethyl ethanolamine and hydrochloride thereof have high yield and high purity, and have high quality.
Use of a Catalytic Chiral Leaving Group for Asymmetric Substitutions at sp3-Hybridized Carbon Atoms: Kinetic Resolution of β-Amino Alcohols by p-Methoxybenzylation
Kuroda, Yusuke,Harada, Shingo,Oonishi, Akinori,Kiyama, Hiroki,Yamaoka, Yousuke,Yamada, Ken-Ichi,Takasu, Kiyosei
supporting information, p. 13137 - 13141 (2016/10/30)
A catalytic strategy was developed for asymmetric substitution reactions at sp3-hybridized carbon atoms by using a chiral alkylating agent generated in situ from trichloroacetimidate and a chiral phosphoric acid. The resulting chiral p-methoxybenzyl phosphate selectively reacts with β-amino alcohols rather than those without a β-NH functionality. The use of an electronically and sterically tuned chiral phosphoric acid enables the kinetic resolution of amino alcohols through p-methoxybenzylation with good enantioselectivity.
Synthesis of chiral oxazolidinone derivatives through lipase-catalyzed kinetic resolution
Zhang, Yan,Zhang, Yang,Ren, Yansong,Ramstr?m, Olof
, p. 29 - 34 (2015/09/15)
The synthesis of enantioenriched oxazolidinone derivatives through lipase-catalyzed kinetic resolution is described. The synthesis comprised a two-step, cascade acylation in one pot, resulting in a range of oxazolidinone derivatives in good yields and exc
Optimization of immobilization conditions of Mucor miehei lipase onto Florisil via polysuccinimide spacer arm using response surface methodology and application of immobilized lipase in asymmetric acylation of 2-amino-1-phenylethanols
Yildirim, Deniz,Tuekel, S. Seyhan,Alptekin, Oezlem,Alagoez, Dilek
, p. 91 - 103 (2014/01/17)
In this study, the immobilization of Mucor miehei lipase onto Florisil support via polysuccinimide spacer arm was scrutinized by using a 3-factor and 3-level Box-Behnken design. The independent parameters were immobilization pH, immobilization time and initial lipase concentration and the response was the specific activity of immobilized lipase. A quadratic equation was used to explain the relationship between the response and independent parameters. After analysis of variance test, coefficient of determination and adjusted coefficient of determination values were estimated as 0.98 and 0.94, respectively. The optimal immobilization pH, immobilization time and initial lipase concentration were determined as 6.0, 7 h and 1.1 mg mL-1, respectively, after desirability analysis. The specific activity values for three individual experiments were observed as 25.88 ± 0.73, 26.06 ± 0.47 and 25.96 ± 0.52 U mg protein-1 under the optimized conditions. The hydrolytic activities of free and immobilized lipase preparations were characterized using p-nitrophenyl palmitate as substrate. The esterification activity of immobilized lipase preparation was evaluated by asymmetric acylation of 2-(methylamino)-1-phenylethanol, 2-(ethylamino)-1- phenylethanol, 2-(butylamino)-1-phenylethanol, and 2-(hexylamino)-1- phenylethanol with vinyl acetate. The acylation protocol was optimized in terms of the effects of initial water amount, reaction temperature, molar ratio of amino alcohol to vinyl acetate, biocatalyst loading, organic medium and kind of lipases used. The developed protocol provided a facile methodology for the preparation of enantiopure 2-amino-1-phenylethanols which may be used as potential new β-adrenergic receptor antagonists.
Immobilized Pseudomonas sp. lipase: A powerful biocatalyst for asymmetric acylation of (±)-2-amino-1-phenylethanols with vinyl acetate
Yildirim, Deniz,Tükel, S. Seyhan
, p. 819 - 830 (2013/07/27)
Pseudomonas sp. lipase was immobilized onto glutaraldehyde-activated Florisil support via Schiff base formation and stabilized by reducing Schiff base with sodium cyanoborohydride. The immobilization performance was evaluated in terms of bound
A simple two-step synthesis of 2-(alkylamino)-1-arylethanols, including racemic adrenaline, from aromatic aldehydes via 5-aryloxazolidines
Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Ya.
, p. 5869 - 5872 (2013/10/21)
Benzaldehydes react smoothly with nonstabilized azomethine ylides, generated in situ from sarcosine/formaldehyde or N-(methoxymethyl)-N- (trimethylsilylmethyl)benzylamine, to give 5-aryloxazolidines as intermediates. These were converted into 2-(alkylamino)-1-arylethanols in good yields by simple heating in methanol with hydrochloric acid, or by treatment with hydrazine hydrate in ethanol.
Asymmetric hydrogenation of α-primary and secondary amino ketones: Efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine
Shang, Gao,Liu, Duan,Allen, Scott E.,Yang, Qin,Zhang, Xumu
, p. 7780 - 7784 (2008/04/03)
Two ss-receptor agonists (-)-denopamine and (-)-arbutamine were prepared in good yields and enantioselectivities by asymmetric hydrogenation of unprotected amino ketones for the first time by using Rh catalysts bearing electron-donating phosphine ligands. A series of α-primary and secondary amino ketones were synthesized and hydrogenated to produce various 1,2-amino alcohols in good yields and with good enantioselectivies. This Rh electron-donating phosphine-catalyzed asymmetric hyderogenation repI resents one of the most promising and convenient approaches towards the asymmetric synthesis of chiral amino alcohols.
