29194-04-5Relevant academic research and scientific papers
Method for Ir/f-amphox high-efficiency synthesis of chiral α- C-amino alcohol by virtue of catalytic oxidation 1,2- of P-aminoketone by using one-aminoketone
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Paragraph 0028-0033, (2020/01/03)
The invention discloses a method for efficiently synthesizing chiral 1,2-amino alcohol by catalyzing alpha-aminoketone through Ir/f-amphox. A ligand f-amphox used by the method can be more easily synthesized; the reaction has the characteristics of enanti
Reaction of 5-aryloxazolidines with arylmagnesium bromides as a new route to N-benzyl-β-hydroxyphenethylamines as starting materials for the preparation of 4-aryl-1,2,3,4-tetrahydroisoquinolines
Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Ya.
, p. 2699 - 2702 (2013/06/26)
Benzaldehydes react smoothly with the non-stabilized azomethine ylide derived from sarcosine and formaldehyde to form 5-aryloxazolidines as intermediates, which undergo ring-opening to give N-benzyl-β- hydroxyphenethylamines in good yields by the action o
4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors
Pechulis, Anthony D.,Beck, James P.,Curry, Matt A.,Wolf, Mark A.,Harms, Arthur E.,Xi, Ning,Opalka, Chet,Sweet, Mark P.,Yang, Zhicai,Vellekoop, A. Samuel,Klos, Andrew M.,Crocker, Peter J.,Hassler, Carla,Laws, Mia,Kitchen, Douglas B.,Smith, Mark A.,Olson, Richard E.,Liu, Shuang,Molino, Bruce F.
, p. 7219 - 7222 (2013/01/15)
Novel 4-phenyl tetrahydroisoquinolines that inhibit both dopamine and norepinephrine transporters were designed and prepared. In this Letter, we describe the synthesis, in vitro activity and associated structure-activity relationships of this series. We also report the ex vivo NET occupancy of a representative compound, 41.
Borrowing hydrogen methodology for amine synthesis under solvent-free microwave conditions
Watson, Andrew J. A.,Maxwell, Aoife C.,Williams, Jonathan M. J.
supporting information; experimental part, p. 2328 - 2331 (2011/05/17)
Application of microwave heating to the Borrowing Hydrogen strategy to form C-N bonds from alcohols and amines is presented, removing the need for solvent and reducing the reaction times while still yielding results comparable with those using thermal heating.
Direct syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines via hydroamination of enol carbamates
Crecente-Campo, José,Vázquez-Tato, M. Pilar,Seijas, Julio A.
experimental part, p. 2655 - 2659 (2009/06/20)
An efficient and simple procedure for the syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines has been developed. The approach uses easily available starting materials and requires just three steps. The hydroamination of an enol carbamate is the key step. This general and direct method has been applied to the total synthesis of the natural alkaloid cherylline and to biologically active 3-benzoazepines as well.
A New Synthesis of 1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines
Venkov, Atanas P.,Vodenicharov, Daniel M.
, p. 253 - 255 (2007/10/02)
1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines 6 are obtained from aromatic aldehydes 1, methyl amine and α-haloacetophenones 2 in the presence of sodium borohydride followed by cyclization with sulfuric acid and zinc in methanol.
Kinetic Resolution of Racemic β-Hydroxy Amines by Enantioselective N-Oxide Formation
Miyano, Sotaro,Lu, Linda D.-L.,Viti, Steven M.,Sharpless, K. Barry
, p. 4350 - 4360 (2007/10/02)
A practical and fairly general procedure for the kinetic resolution of β-hydroxy tertiary amines is described.It involves the selective oxidation of one enantiomer to the N-oxide by using tert-butyl hydroperoxide (TBHP) and a chiral catalyst prepared by mixing 2 parts of titanium isopropoxide (Ti(O-i-Pr)4 and 1.2 parts of either (+)- or (-)-diisopropyl tartrate (DIPT).The product N-oxide and the unreacted amino alcohol are then easily separated by trituration or organic/aqueous solvent extractions, and chromatography is avoided.The oxidations are generally run to 60percent conversion and the results for 21 different amino alcohols are given.The enantiomeric excess of the slow reacting (i.e., recovered) enantiomer of the amino alcohol often exceeds 90percent.Among the more interesting substrates are the natural product ubine (95percent ee) (18), N-methylephedrine (95percent ee) (15), N-methylpseudoephedrine (93percent ee) (16), cis-2-(dimethylamino)cyclohexanol (>95percent ee) (13), trans-2-(dimethylamino)cyclohexanol (92percent ee) (12), N-benzylbevantolol (85percent ee) (27), and N-benzylpropranolol (32percent ee) (21).The latter two examples are β-blocker precursors.One of the most important characteristics of this new route to enantiomerically pure β-hydroxy amines is its predictability.Thus, in all cases examined to date, when using (+)-DIPT the absolute configuration at the carbinol center in the slow reacting enantiomer is always the same .A study of how the titanium/tartrate ratio, water, catalyst/substrate ratio, and temperature effect this reaction is discussed.
