117857-52-0Relevant articles and documents
Optical resolution of rimantadine
Han, Jianlin,Takeda, Ryosuke,Sato, Tatsunori,Moriwaki, Hiroki,Abe, Hidenori,Izawa, Kunisuke,Soloshonok, Vadim A.
, (2019)
This work discloses a new procedure for the resolution of commercially available racemic rimantadine hydrochloride to enantiomerically pure (S)-rimantadine using (R)-phenoxypropionic acid as a recyclable resolving reagent. Good chemical yields, operational ease, and low-cost structure underscore the preparative value of this method for the production of enantiomerically pure rimantadine for medicinal or synthetic studies.
Titanium(IV) mediated reductive aminations of 1-adamantyl methyl ketone: facile preparation of potential antiviral agents rimantadine and its analogues
Bhattacharyya, Sukanta
, p. 1845 - 1848 (1995)
A preparatively efficient, mild method for the synthesis of rimantadine and its analogues via novel reductive aminations of 1-adamantyl methyl ketone titanium(IV) isopropoxide and sodium borohydride is reported.
Approaches to primary tert-alkyl amines as building blocks
Tzitzoglaki, Christina,Drakopoulos, Antonios,Konstantinidi, Athina,Stylianakis, Ioannis,Stampolaki, Marianna,Kolocouris, Antonios
, (2019/07/10)
Primary tert-alkyl amines include analogues of amantadine, a fragment commonly linked to pharmacophoric groups to enhance biological activity. The preparation of primary tert-alkyl amines is considered to be a difficult problem. Four synthetic procedures, some of which have been previously reported for the synthesis of amines with primary (RCH2NH2) or secondary (RR'CHNH2) alkyl and/or aryl groups, were tested for the synthesis of primary tert-alkyl amines (RR′R″CNH2) in aliphatic series including adamantane adducts. These procedures included the formation and reduction of tert-alkyl azides, the Ritter reaction in standard and modified conditions, the addition of organometallic reagents to N-tert-butyl sulfinyl ketimines and one-pot reactions between nitriles and organometallic reagents in the presence of a Lewis acid, Τi(iPrO)4 or CeCl3. These synthetic routes are unexplored for primary tert-alkyl amines. Studies on the synthetic routes for primary tert-alkyl amines are currently lacking. The reaction conditions and substrate limitations were studied for each procedure, with the first procedure being the most general and applicable also for compounds bearing bulky adducts.
Preparation method of rimantadine hydrochloride
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Paragraph 0011-0012, (2019/06/08)
The invention belongs to the filed of preparation of chemical intermediates, and specifically relates to a preparation method of rimantadine hydrochloride. 1-adamantyl methy ketone is used as a starting material, then reacts with hydroxylamine hydrochloride, and catalyzed and hydrogenated to obtain rimantadine hydrochloride with a high yield. In the reaction of preparing the target object, oxime is prepared firstly, then is catalyzed and hydrogenated. Despite of additional oxime-preparing reaction, the reaction yield in each step is high. The preparation method has the characteristics of highyield, cheap raw materials, simple technical treatment and quality products, thus having certain application value.
