- Direct catalytic synthesis of unprotected 2-amino-1-phenylethanols from alkenes by using iron(II) phthalocyanine
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Aryl-substituted amino alcohols are privileged scaffolds in medicinal chemistry and natural products. Herein, we report that an exceptionally simple and inexpensive FeII complex efficiently catalyzes the direct transformation of simple alkenes into unprotected amino alcohols in good yield and perfect regioselectivity. This new catalytic method was applied in the expedient synthesis of bioactive molecules and could be extended to aminoetherification.
- Legnani, Luca,Morandi, Bill
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supporting information
p. 2248 - 2251
(2016/02/18)
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- Cyclic trans-β-amino alcohols: Preparation and enzymatic kinetic resolution
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Enantioenriched cyclic β-amino alcohols, trans-2-aminocyclohexanols (ee, >99%), trans-2-aminocyclopentanols (ee, >99%), trans-1-amino-2- indanols (ee, >99%) and trans-2-amino-1-indanols (ee, ～98%) were prepared in high yields via an Arthrobacter sp. Lipase/PLAP catalyzed kinetic resolution of racemic phthalimido acetates. The addition of toluene as a co-solvent dramatically improved the hydrolysis and enantioselectivity, whereas for indanols, substrate immobilization on Celite improved the efficacy of the kinetic resolution.
- Rouf, Abdul,Gupta, Pankaj,Aga, Mushtaq A.,Kumar, Brijesh,Parshad, Rajinder,Taneja, Subhash C.
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p. 2134 - 2143
(2012/05/04)
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- Bicyclic pyrrolyl amides as glucogen phosphorylase inhibitors
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Heterocyclic amide derivatives, of formula (I): wherein —X-Y-Z- is selected from —S—CR4═CR5—, —CR4═CR5—S—, —O—CR4═CR5—, —CR4═CR5—O—, —N═CR4—S—, —S—CR4═N—, —NR6—CR4═CR5— and —CR4═CR5—NR6—; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof; (with provisos); possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.
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- Optimization and scale-up of a novel process for 2-aminoindan hydrochloride production
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The need for an economical process for producing 2-aminoindan hydrochloride, a key starting material in manufacturing novel bioactive molecules, motivated development of a novel synthetic route using an inexpensive reactant, ninhydrin. The synthesis, involving oximation of ninhydrin followed by catalytic reduction of the resulting oxime intermediate to give 2-aminoindan, was demonstrated successfully, and a product purification scheme was developed to isolate 2-aminoindan as the hydrochloride salt form. Subsequent process development optimized the reduction step by identifying regimes of fast and slow reaction (corresponding to reduction of oxime and diketone functions, respectively), and tailoring reaction conditions to use mild conditions during the fast exothermic regime to ensure process safety followed by more severe conditions for the slower reaction. The process was successfully scaled up 100-fold in a pilot plant, with excellent yield and product quality agreement between laboratory and pilot plant.
- Roche, Didier,Sans, David,Girgis, Michael J.,Prasad, Kapa,Repic, Oljan,Blacklock, Thomas J.
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p. 167 - 175
(2013/09/07)
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- Enzymatic hydroxylation by dopamine β-hydroxylase
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The three-dimensional aspects of the chemistry of dopamine β-hydroxylase (DBH) was studied through a conformationally-restricted substrate analog approach. We found that the DBH-catalyzed hydroxylation of 2-aminoindane (1) exclusively produced the trans-(1S,2S)-2-amino-1-indanol (4S) (93% ee) in contrast to the stereochemical course of the pro-R hydroxylation of the DBH/phenethylamine reaction. Studies with stereospecifically deuterium labeled 2-aminoindanes 2 and 3 show that the production of (1S)-aminoindanol 4S is the result of stereospecific pro-S hydrogen abstraction followed by the oxygen binding with overall retention of configuration. On the basis of these findings, we propose a model for the interaction of the phenethylamine substrates with the enzyme.
- Mitrochkine, Anton A.,Eydoux, Frank,Gil, Gerard,Reglier, Marius
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p. 1171 - 1176
(2007/10/03)
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- Stereoselective synthesis of 1,2-amino alcohols by asymmetric borane reduction of α-oxoketoxime ethers
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Asymmetric reduction of α-oxoketoxime ethers with the reagents prepared in situ from trimethyl borate and chiral amino alcohols derived from either L-proline or α-pinene was investigated. Both cyclic and acyclic α- oxoketoxime ethers were reduced to afford the corresponding chiral 1,2amino alcohols with high enantioselectivities.
- Masui, Moriyasu,Shioiri, Takayuki
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p. 5195 - 5198
(2007/10/03)
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- INDANE AND TETRAHYDRONAPHTHALENE DERIVATIVES AS CALCIUM CHANNEL ANTAGONISTS
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This invention describes the use of aminoindane and amino-tetrahydronaphthalene derivatives of general formula (I) STR1 in which Ar, X, R 1, R 2 and n are defined in claim 1, for the manufacture of a medicament for the treatment of disorders in which a calcium channel antagonist is indicated. Novel compounds falling within formula (I) are also claimed.
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- Synthesis of Enantiomerically Pure cis and trans-2-Amino-1-indanol
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Enantiomerically pure cis and trans-2-amino-1-indanols 1 and 2 were synthesized via a highly enetioslective lipase catalyzed transestrification of racemic cis-2-azido-1-indanol 3.
- Mitrochkine, Anton,Gil, Gerard,Reglier, Marius
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p. 1535 - 1538
(2007/10/02)
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- Synthesis of 4-Aryl-2-benzazepine-1,5-diones by Photocyclization of N-(2-Arylethyl)phthalimides
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The photocyclization of N-(2-arylethyl)phthalimides to 4-aryl-2-benzazepine-1,5-diones is described.We found that the presence of electron donating substituents on the aryl ring (as in 10a and b) is necessary for the cyclization process to occur.The procedure also allowed synthesis of 2-benzazepinediones with a carboxylate group at C3 (11c and d) which were obtained as 1:1 mixture of diastereoisomers.The results of irradiating phthalimides 12, which bear an oxygenated substituent at the benzylic position, depended on the nature of the substituent.Attempts to photocyclize N-(indan-2-yl)phthalimides 16 and the electron-rich phthalimide 23 failed.
- Paleo, M. Rita,Dominguez, Domingo,Castedo, Luis
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p. 3627 - 3638
(2007/10/02)
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- COPPER(II) IN ORGANIC SYNTHESIS. X. THE IMPORTANCE OF STERIC HINDRANCE IN THE DESIGN OF CHIRAL TRIDENTATE LIGAND COPPER(II) CATALYSTS FOR ENANTIOSELECTIVE MICHAEL REACTIONS
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Several copper(II) complexes with tridentate chiral ligands derived from 2-substituted 2-aminoethanols have been tested as catalysts for enantioselective Michael reactions.The degree of enantioselection increases with the increase of the steric hindrance of the substituents and the best result (65percent e.e.) was obtained with the benzyl-substituted catalyst.A comparison of these results with those obtained with complexes derived from 2-amino-1-indanols gives useful information about the requirements for the optimization of the catalyst design.
- Desimoni, Giovanni,Faita, Giuseppe,Mellerio, Giorgio,Righetti, Pier Paolo,Zanelli, Claudio
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p. 269 - 273
(2007/10/02)
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