178152-48-2Relevant articles and documents
Method for preparing (1R, 3S)-3-aminocyclopentanol hydrochloride
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, (2021/03/31)
The invention discloses a method for preparing (1R, 3S) 3-aminocyclopentanol hydrochloride, belongs to the field of organic chemical synthesis, and provides a process route to overcome the defects ofhigh price, difficulty in chiral control and the like in the prior art. The process route comprises the following steps: 1) oxidizing tert-butyl carbonate hydroxylamine into tert-butyl carbonate nitrosyl under the catalysis of copper chloride and 2-ethyl-2-oxazoline, then carrying out a hetero Diels-Alder reaction with cyclopentadiene in situ; 2) selectively reducing nitrogen-oxygen bonds in a zinc powder-acetic acid reaction system; 3) under the catalysis of lipase, reacting with vinyl acetate to optically and selectively realize chiral resolution; 4) reducing double bonds through palladium carbon hydrogenation; 5) under the alkaline condition of lithium hydroxide-methanol, performing deacetylation protection; and 6) removing tert-butyl carbonate protection in a hydrogen chloride isopropanol acid solution prepared from acetyl chloride and isopropanol in situ, and forming hydrochloride in situ to obtain a target product. The synthetic method has the beneficial effects that the synthetic method has the characteristics of novel and short route, high optical purity, low cost and the like.
Addition of Lithium Anion of (Acetylmethylene)triphenylphosphorane to Nonracemic Sulfinimines: Total Synthesis of (+)-241D and Formal Total Synthesis of (+)-Preussin
Khandare, Sopan P.,Prasad, Kavirayani R.,Reddy, Polimera Obula
supporting information, p. 7273 - 7277 (2020/10/02)
The addition of lithium anion of (acetylmethylene)triphenylphosphorane to nonracemic sulfinimines was investigated. It was found that the addition proceeded with good diastereoselectivity and further reaction of the formed sulfinimidophosphorane with seve
Novel Imidazo[4,5-c]Quinoline And Imidazo[4,5-c][1,5]Naphthyridine Derivatives As LRRK2 Inhibitors
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, (2017/04/04)
The present invention provides novel imidazo[4,5-c]quinoline and imidazo[4,5-c][1,5]naphthyridine derivatives of Formula (I), and the pharmaceutically acceptable salts thereof wherein R1, R1a, R1b, R2, R4, R5, R6, X and Z are as defined in the specification. The invention is also directed to pharmaceutical compositions comprising the compounds of Formula (I) and to use of the compounds in the treatment of diseases associated with LRRK2, such as neurodegenerative diseases including Parkinson's disease or Alzheimer's disease, cancer, Crohn's disease or leprosy.
POLYFLUORINATED COMPOUNDS ACTING AS BRUTON TYROSINE KINASE INHIBITORS
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Paragraph 0498; 0499, (2016/08/17)
Described herein is a novel series of multi-fluoro-substituted pyrazolopyrimidine compounds or salts thereof. These compounds are Bruton's tyrosine kinase (BTK) inhibitors. These compounds may possess better BTK inhibition selectivity and pharmacokinetic properties. Disclosed herein are the synthesis methods of these compounds. Disclosed herein are novel synthesis methods of the multi-fluoro-substituted benzophenone and substituted phenoxy benzene. Also disclosed are pharmaceutical compositions comprising the BTK inhibitors described herein. The present invention also relates to pharmaceutical formulations comprising the compounds described herein as active ingredients. The present invention also includes the therapeutic methods by administering the BTK inhibitors and their formulations to treat and inhibit autoimmune disease, hypersensitivity disease, inflammatory diseases and cancer.
Asymmetric synthesis of cis-aminocyclopentenols, building blocks for medicinal chemistry
Zaed, Ahmed M.,Grafton, Mark W.,Ahmad, Sajjad,Sutherland, Andrew
, p. 1511 - 1515 (2014/03/21)
A highly efficient one-pot multistep process involving an asymmetric Pd(II)-catalyzed Overman rearrangement and a Ru(II)-catalyzed ring-closing metathesis reaction has been developed for the preparation of (R)- or (S)-aminocyclopenta-2-enes. The rapid strategy employed and the relatively mild conditions of the one-pot process allowed the multigram synthesis of the carbocycles in high enantiomeric excess (92% ee). The synthetic utility of these compounds was demonstrated by the stereoselective incorporation of hydroxyl groups, generating cis-4- and cis-5-aminocyclopenta-2-en-1-ols, important building blocks for medicinal chemistry.
Enantioselective syntheses of carbocyclic nucleosides 5′- homocarbovir, epi-4′-homocarbovir, and their cyclopropylamine analogs using facially selective Pd-mediated allylations
Tardibono Jr., Lawrence P.,Miller, Marvin J.,Balzarini, Jan
scheme or table, p. 825 - 829 (2011/03/19)
Carbocyclic nucleosides (-)-5′-homocarbovir and (+)-epi-4′- homocarbovir were prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct. A kinetic enzymatic resolution generated an enantiopure aminocyclopentenol and Pd(0)-mediated decarboxylativ
Palladium-catalyzed decarboxylative rearrangements of allyl 2,2,2-trifluoroethyl malonates: direct access to homoallylic esters
Tardibono Jr., Lawrence P.,Patzner, Jerod,Cesarlo, Cara,Miller, Marvin J.
supporting information; scheme or table, p. 4076 - 4079 (2009/12/06)
Homoallylic esters are obtained In a single transformation from allyl 2,2,2-trifluoroethyl malonates by using a Pd(O) catalyst. Facile decarboxylation of allyl 2,2,2-trifluoroethyl malonates is attributed to a decrease in pK a compared to allyl
Titanocene(III) chloride-mediated reductions of oxazines, hydroxamic acids, and N-hydroxy carbamates
Cesario, Cara,Tardibono Jr., Lawrence P.,Miller, Marvin J.
supporting information; experimental part, p. 448 - 451 (2009/04/07)
(Chemical Equation Presented) Titanocene(III) chloride (Cp 2TiCl), generated in situ, reduces N-O bonds of various substrates in good to excellent yields (72-95%). Reactions may be performed with stoichiometric Cp2TiCl or with cataly
Total synthesis of (-)-agelastatin A
Yoshimitsu, Takehiko,Ino, Tatsunori,Tanaka, Tetsuaki
supporting information; experimental part, p. 5457 - 5460 (2009/06/06)
(Chemical Equation Presented) A new route to (-)-agelastatin A is reported. The requisite nitrogen functionalities of the agelastatin core have been installed by intramolecular aziridination of an azidoformate and subsequent regioselective azidation, lead
Concise syntheses of enantiomerically pure protected 4-hydroxypyroglutamic acid and 4-hydroxyproline from a nitroso-cyclopentadiene cycloadduct
Huang, Weiqiang,Miller, Marvin J.
experimental part, p. 2835 - 2838 (2009/06/28)
O-TBS-protected methyl trans-4-hydroxypyroglutamate and methyl trans-4-hydroxyproline ester were synthesized from nitroso-cyclopentadiene Diels-Alder cycloadducts. Enzymatic resolution of the key intermediate, 4-amino-cyclopent-2-enol, provides access to both l- and d-amino acids.
