1222073-98-4Relevant academic research and scientific papers
Synthesis of 3-vinylphenyl ethyl(methyl)carbamate: A potential human metabolite of rivastigmine
Xu, Guanhong,Ma, Teng,Yang, Jing,Wang, Fengliang,Zhang, Hongjuan,Wang, Xiuzhen,Li, Fei
, p. 3499 - 3500 (2013)
Convenient and efficient syntheses of 3-vinylphenyl ethyl (methyl) carbamate, one of potential metabolites from rivastigmine, has been developed. The overall yield is higher than 30% and represents the first direct synthesis of this metabolite from rivast
Chemoenzymatic synthesis of rivastigmine via dynamic kinetic resolution as a key step
Han, Kiwon,Kim, Cheolwoo,Park, Jaiwook,Kim, Mahn-Joo
, p. 3105 - 3108 (2010)
A practical and efficient procedure for the synthesis of rivastigmine was developed. This procedure includes dynamic kinetic resolution using a polymer-bound ruthenium complex and a lipase in combination as a key step. Enantiopure (-)-rivastigmine was obtained from commercially available 3′-hydroxyacetophenone via five steps in overall 57% yield.
Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts
Oestreich, Martin,Seliger, Jan
supporting information, p. 247 - 251 (2020/10/29)
A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.
SYNTHESIS OF NOVEL INTERMEDIATE(S) FOR PREPARING RIVASTIGMINE
-
, (2020/04/10)
The present invention relates to novel intermediate(s), which are useful for the preparation of Rivastigmine compound of formula (I) and its pharmaceutically acceptable salts. The present invention further relates to the processes for the preparation of such novel intermediate(s) and preparation of Rivastigmine using such novel intermediate(s).
A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions
Huy, Peter H.,Filbrich, Isabel
, p. 7410 - 7416 (2018/04/30)
A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.
Phototransformation of the drug rivastigmine: Photoinduced cleavage of benzyl-nitrogen sigma bond
Temussi, Fabio,Passananti, Monica,Previtera, Lucio,Iesce, Maria Rosaria,Brigante, Marcello,Mailhot, Gilles,Dellagreca, Marina
experimental part, p. 1 - 6 (2012/09/07)
The photochemical behaviour of rivastigmine has been investigated under UV-B irradiation by HPLC and NMR. Kinetic data have been obtained irradiating aqueous solutions (5 × 10-5 M). For mechanistic purposes and products studies irradiation has
Achiral bis-imine in combination with CoCI2: A remarkable effect on enantioselectivity of lipasemediated acetylation of racemic secondary alcohol
Arunkumar,Appi Reddy,Sravan Kumar,Vijaya Kumar,Chandrasekhar,Rajender Kumar,Pal, Manojit
supporting information; experimental part, p. 1174 - 1179 (2011/03/22)
A bis-imine (prepared via a new FeCl3-based method) in combination with CoCl2 facilitated lipase-mediated acetylation of the (R)-isomer of a racemic benzylic secondary alcohol with 91% ees. The methodology was used for the preparation of the known drug rivastigmine.
NOVEL PROCESSES FOR THE PREPARATION OF AMINOALKYL PHENYLCARBAMATES
-
Page/Page column 18, (2010/02/12)
The present invention relates to a process for preparing an aminoalkyl phenylcarbamate (4), comprising the steps of converting a hydroxy phenyl ketone (2) to a phenylcarbamate ketone (3), and converting the phenylcarbamate ketone (3) to the desired aminoalkyl phenylcarbamate (4). Optionally the aminoalkyl phenylcarbamate (4) may be resolved into its enantiomers and/or converted into a pharmaceutically acceptable acid addition salt. The invention further relates to aminoalkyl phenylcarbamates (4) and pharmaceutically acceptable salts prepared by the above process, in particular, to rivastigmine (1) and rivastigmine hydrogen tartrate (9). The aminoalkyl phenylcarbamates (4) may be comprised in pharmaceutical compositions. The invention further relates to a method of inhibiting acetylcholine esterase or treating dementia, senile dementia, Alzheimer's disease, Huntington's chorea, tardive dyskinesias, hyperkinesia, a confusion disorder, ataxia, Friedrich's ataxia, Down's syndrome, mania or an acute confusion disorder, using the aminoalkyl phenylcarbamates (4) of the present invention.
