134108-76-2Relevant academic research and scientific papers
Designing enzymatic resolution of amines
Takayama, Shuichi,Lee, Shelly T.,Hung, Shang-Cheng,Wong, Chi-Huey
, p. 127 - 128 (1999)
A new strategy, utilizing IR and mass spectrometry, has been developed to design appropriate reagents and reaction conditions for enantioselective enzymatic protection of amines with readily removable protecting groups.
Synthesis of Aminomethylene- gem-bisphosphonates Containing an Aziridine Motif: Studies of the Reaction Scope and Insight into the Mechanism
Cheviet, Thomas,Peyrottes, Suzanne
, p. 3107 - 3119 (2021/02/05)
A broad range of N-carbamoylaziridines were obtained and then treated by the diethyl phosphonate anion to afford α-methylene-gem-bisphosphonate aziridines. Study of the reaction's scope and additional experiments indicates that the transformation proceeds via a new mechanism involving the chelation of lithium ion. This last step is crucial for the reaction to occur and disfavors the aziridine ring-opening. A phosphonate-phosphate rearrangement from a α-hydroxybisphosphonate aziridine intermediate is also proposed for the first time. This reaction provides a simple and convenient method for the synthesis of a highly functionalized phosphonylated aziridine motif.
A method for preparing weinaweina kalland hydrochloride (by machine translation)
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Paragraph 0048; 0051-0052, (2017/11/27)
The invention discloses a method for preparing weinaweina kalland hydrochloride. The method to selectively amino protection, nucleophilic addition, nucleophilic substitution, deprotected, cyclized, reduction, into a salt by the reaction of the compound Wina carland hydrochloride. And after nuclear magnetic analysis test technology confirm its structure. It adopts the cheap and easily obtained starting materials to prepare, preparation method has advantages of simple operation, mild condition, easy industrialized production and the like, and avoids the use of heavy metal, is beneficial to the development of the oral. (by machine translation)
Purification method of vernakalant hydrochloride
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Paragraph 0048-0049, (2017/01/12)
The invention discloses a purification method of vernakalant hydrochloride. The method comprises the steps of preparation of a vernakalant hydrochloride crude product and purification through the process of alkalinization, nonpolar solvent extraction, acidification and mixed solvent pulping, and thus a qualified product is obtained. The preparation method is simple in operation, mild in condition and easy for industrialized production, and the purity of the product reaches 99.9 percent, and the total impurity and single impurity are both less than 0.1 percent, so that the quality requirements for preparing medicine can be reached, and at the same time, the usage of heavy metal is avoided, and the development of injection forms is facilitated.
Enhanced rate and selectivity by carboxylate salt as a basic cocatalyst in chiral N-heterocyclic carbene-catalyzed asymmetric acylation of secondary alcohols
Kuwano, Satoru,Harada, Shingo,Kang, Bubwoong,Oriez, Raphael,Yamaoka, Yousuke,Takasu, Kiyosei,Yamada, Ken-Ichi
supporting information, p. 11485 - 11488 (2013/09/02)
The rate and enantioselectivity of chiral NHC-catalyzed asymmetric acylation of alcohols with an adjacent H-bond donor functionality are remarkably enhanced in the presence of a carboxylate cocatalyst. The degree of the enhancement is correlated with the basicity of the carboxylate. With a cocatalyst and a newly developed electron-deficient chiral NHC, kinetic resolution and desymmetrization of cyclic diols and amino alcohols were achieved with extremely high selectivity (up to s = 218 and 99% ee, respectively) at a low catalyst loading (0.5 mol %). This asymmetric acylation is characterized by a unique preference for alcohols over amines, which are not converted into amides under the reaction conditions.
New procedure for the preparation of (1 R,2 R)-2-[(R)-3-(benzyloxy)pyr- rolidin-1-yl]cyclohexanol
Ye, Haiwei,Yu, Chuanming,Zhong, Weihui
experimental part, p. 51 - 56 (2012/04/10)
A novel route to an intermediate of vernakalant, (1R,2R)-2-[(R)-3- (benzyloxy)pyrrolidin-1-yl]cyclohexanol from ethyl (R)-4-chloro-3- hydroxybutanoate is described. It was found that the key intermediate (R)-4-(benzyloxy)-1-[(1R,2R)-2-(tert-butyldimethylsiloxy)cyclohexyl] pyrrolidin-2-one could be isolated with high dia-stereomeric excess (up to 99% de) from its isomer by column chromatography alone, without further chemical resolution. Georg Thieme Verlag Stuttgart. New York.
Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction
Harris, Lawrence,Mee, Simon P. H.,Furneaux, Richard H.,Gainsford, Graeme J.,Luxenburger, Andreas
experimental part, p. 358 - 372 (2011/04/17)
Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.
IMPROVED AMINOHYDROXYLATION OF ALKENES
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Page/Page column 52, (2012/01/06)
The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.
A General Route to the Synthesis of N-Protected 1-Substituted and 1,2-Disubstituted Taurines
Xu, Jiaxi,Xu, Shu
, p. 276 - 282 (2007/10/03)
N-Benzyloxycarbonyl protected α-substituted and αβ- disubstituted taurines were synthesized from olefins and epoxides via N-benzyloxycarbonylamino alcohol thioacetates as key intermediates. They are important sulfur analogues of naturally occurring amino acids and building blocks for the synthesis of α-substituted and α,β- disubstituted β-sulfonopeptides.
Enzymatic resolution of (±)-cis-2-aminocyclopentanol and (±)-cis-2- aminocyclohexanol
Luna, Amparo,Astorga, Covadonga,Fueloep, Ferenc,Gotor, Vicente
, p. 4483 - 4487 (2007/10/03)
(±)-cis-N-Benzyloxycarbonyl-2-aminocyclopentanol was efficiently resolved by O-acylation with Pseudomonas cepacia lipase, as was (±)-cis-N- benzyloxycarbonyl-2-aminocyclohexanol when Candida antarctica lipase was used.
