93601-86-6Relevant academic research and scientific papers
Preparation method of (S)-1, 2, 3, 4-tetrahydro-5-methoxy-N-propyl-2-naphthylamine hydrochloride
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Paragraph 0040; 0060-0068, (2020/07/21)
The invention relates to a preparation method of (S)-1, 2, 3, 4-tetrahydro-5-methoxy-N-propyl-2-naphthylamine hydrochloride, which is characterized by comprising the following steps: step 1, in the presence of a reducing agent, carrying out reductive amination reaction on (S)-1, 2, 3, 4-tetrahydro-5-methoxy-N-((R)-1-benzyl)-2-naphthylamine and propionaldehyde under acidic conditions to obtain a compound II; and step 2, carrying out a catalytic hydrogenation reaction on the compound II in the presence of a hydrogenation catalyst, and carrying out salifying in the presence of a salifying agent to obtain (S)-1, 2, 3, 4-tetrahydro-5-methoxy-N-propyl-2-naphthylamine hydrochloride. The invention also relates to the compound II.
Enantioselective Synthesis of β-Aminotetralins via Chiral Phosphoric Acid-catalyzed Reductive Amination of β-Tetralones
Park, Do Young,Kim, Kyung-Hee,Cheon, Cheol-Hong
supporting information, p. 462 - 467 (2017/12/07)
A new protocol for the synthesis of chiral β-aminotetralins has been developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of β-tetralones using a Hantzsch ester as an organic hydride donor. Various chiral β-aminotetralins were obtained in good yields with good to high enantioselectivities. Furthermore, the utility of our new protocol was successfully demonstrated in the enantioselective synthesis of rotigotine. (Figure presented.).
New catalytic route for the synthesis of an optically active tetralone-derived amine for rotigotine
Cobley, Christopher J.,Evans, George,Fanjul, Tamara,Simmonds, Shaun,Woods, Amy
supporting information, p. 986 - 989 (2016/02/18)
Rotigotine is a launched drug for the treatment of Parkinson's disease and restless legs syndrome. The key steps of an alternative route for the synthesis of rotigotine have been demonstrated. Formation of a prochiral enamide, asymmetric hydrogenation of the enamide with high enantioselectivity, and reduction of the resulting amide to an amine have been proved to work successfully. The best conditions screened to date for the asymmetric hydrogenation of enamide 9 to amide 10 were with [(RuCl((R)-T-BINAP))2(μ-Cl)3][NH2Me2] at 25 bar H2 and 30 °C (500:1 S/C ratio, 99% conversion, 91% ee S). Reduction of amide 10 to amine 5 was best achieved with Red-Al giving 95% conversion.
Novel Process for the Preparation of Nitrogen Substituted Aminotetralins Derivatives
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, (2013/05/08)
The present invention provides an alternative synthesis of N-substituted aminotetralines comprising resolution of N-substituted aminotetralins of formula (II), wherein R1, R2 and R3 are as defined for compound of formula (I).
NOVEL PROCESS FOR THE PREPARATION OF NITROGEN SUBSTITUTED AMINOTETRALINS DERIVATIVES
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, (2012/01/13)
The present invention provides an alternative synthesis of N-substituted aminotetralines comprising resolution of N-substituted aminotetralins of formula (II), wherein R1, R2 and R3 are as defined for compound of formula (I).
Practical asymmetric synthesis of bioactive aminotetralins from a racemic precursor using a regiodivergent resolution
Webster, Robert,Boyer, Alistair,Fleming, Matthew J.,Lautens, Mark
supporting information; experimental part, p. 5418 - 5421 (2011/02/26)
Catalyst-controlled asymmetric ring opening of a racemic oxabicyclic alkene leads to two readily separable regioisomeric products both in excellent ee. A cationic Rh catalyst, with added NH4BF4 to modulate reactivity, was required to obtain synthetically useful yields. The utility of each substituted aminotetralin product has been demonstrated by their conversion to different biologically relevant molecules in a highly efficient and practical manner.
Further delineation of hydrophobic binding sites in dopamine D 2/D3 receptors for N-4 substituents on the piperazine ring of the hybrid template 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5, 6,7,8-tetrahydro-naphthalen-2-ol
Ghosh, Balaram,Antonio, Tamara,Gopishetty, Bhaskar,Reith, Maarten,Dutta, Aloke
experimental part, p. 5661 - 5674 (2010/10/01)
Here we report a structure-activity relationship (SAR) study of analogues of 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro- naphthalen-2-ol. Our SAR is focused on introduction of various substitutions in the piperazine ring of the hybrid template. The goal behind this study is to delineate the nature of the binding pocket for N-aryl substitution in the piperazine ring by observing the effect of various hydrophobic and other heteroaromatic substitutions on binding affinity (Ki), as measured with tritiated spiperone and HEK-293 cells expressing either D2 or D3 receptors. Functional activity of selected compounds was assessed with the GTPγS binding assay. Compound 8d was the most selective for the D3 receptor in the spiperone binding assay. An interesting similarity in binding affinity was observed between isoquinoline derivative D-301 and the 2-substituted pyridine derivative 8d, suggesting the importance of relative spatial relationships between the N-atom of the ligand and the molecular determinants of the binding pocket in D2/D3 receptors. Functional activity assays demonstrated high potency and selectivity of (+)-8a and (-)-28b (D2/D3 (ratio of EC50): 105 and 202, respectively) for the D3 receptor and both compounds were more selective compared to the reference drug ropinirole (D2/D3 (ratio of EC50): 29.5).
