308273-66-7

Upstream product

• 268556-72-5 4-methoxybenzyl(1-phenylethylidene)amine 
• 82319-42-4 (S)-N-(4-methoxybenzylidene)-α-methylbenzylamine 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 2393-23-9 4-methoxy-benzylamine 
• 98-86-2 acetophenone 
• 793713-91-4 4-cyano-N-(4-methoxybenzyl)benzenesulfonamide 
• 123-11-5 4-methoxy-benzaldehyde 
• 202123-13-5 (4-methoxyphenyl)-N-(1-phenylethylidene)methanamine 
• 135820-59-6 (S)-N-(4-Methoxybenzylidene)-1-phenylethanamine 

Downstream Products

• 308273-75-8 (S)-6-Chloro-3-[(4-methoxy-benzyl)-((S)-1-phenyl-ethyl)-amino]-hexanoic acid ethyl ester 
• 453556-43-9 methyl (3S,αS)-3-[N-(p-methoxybenzyl)-N-(α-methylbenzyl)amino]butyrate 
• 600700-26-3 (3R)-2-p-methoxybenzyl-7,8-dimethoxy-1-oxo-3-phenyl-1,2,3,4-tetrahydrobenzo[b]-1,6-naphthyridine 
• 600700-24-1 methyl (3R)-3-[N-(p-methoxybenzyl)-N-((ethoxycarbonyl)acetyl)amino]-3-phenylpropanoate 
• 600700-25-2 (6R)-6-phenyl-1-(p-methoxybenzyl)piperidine-2,4-dione 
• 600700-23-0 methyl (3R)-3-[N-(p-methoxybenzyl)amino]-3-phenylpropanoate 
• 453556-47-3 (3S)-2-p-methoxybenzyl-3-methyl-7,8-dimethoxy-1-oxo-1,2,3,4-tetrahydrobenzo[b]-1,6-naphthyridine 
• 453556-45-1 methyl (3S)-3-[N-(p-methoxybenzyl)-N-((ethoxycarbonyl)acetyl)amino]butyrate 
• 453556-46-2 (6S)-1-(p-methoxybenzyl)-6-methylpiperidine-2,4-dione 
• 453556-44-0 methyl (3S)-3-[N-(p-methoxybenzyl)amino]butyrate 
• 918476-51-4 (S,S)-N,N'-bis-(4-methoxybenzyl) N,N'-bis-(1-phenylethyl)-oxalamide 
• 600700-22-9 methyl (3R,αS)-3-[N-(p-methoxybenzyl)-N-(α-methylbenzyl)amino]-3-phenylpropanoate 

Relevant academic research and scientific papers

CHIRAL CATALYST AND METHOD FOR ASYMMETRIC REDUCTION OF AN IMINE

The present disclosure discusses (i) a compound having a chemical formula according to Formula (I), or its enantiomer; and (ii) a compound that is reactive with a hydride to produce a compound having a chemical formula according to Formula (I), or its enantiomer. Formula (I) is: Formula (I) where R1 and R2 are H, optionally substituted C1-C3 alkyl, or linked together to form an optionally substituted C3 or C4 alkyl group; R3 and R3' are H; R4 and R4' are the same, and are optionally substituted C1-C6 alkyl; and R5 and R5' are the same, and are optionally substituted aryl or heteroaryl. In some examples, R4 and R5 are linked, and R4' and R5' are linked, where both linking groups are the same. The present disclosure also discusses methods of asymmetric reduction of an imine, and methods of forming the catalysts and pre-catalysts.

Asymmetric Imine Hydroboration Catalyzed by Chiral Diazaphospholenes

The first use of diazaphospholenes as chiral catalysts has been demonstrated with enantioselective imine hydroboration. A chiral diazaphospholene prepared in a simple three-step synthesis from commercial materials has been shown to achieve the highest enantioselectivity for the hydroboration of alkyl imines with pinacolborane reported to date. Enantiomer ratios of up to 88:12 were obtained with low (2 mol %) catalyst loadings. Twenty examples of asymmetric reduction employing this main-group catalysis protocol, including the synthesis of the pharmaceuticals ent-rasagiline and fendiline, are shown.

4-Cyanobenzenesulfonamides: Amine Synthesis and Protecting Strategy To Compliment the Nosyl Group

4-Cyanobenzenesulfonamides of secondary amines were found to cleave to the parent amine cleanly under the action of thiol and base. This feature readily lends itself to the use of this motif as an amine protecting/activating group within a broader context of amine synthesis. The crystalline sulfonamides could be further elaborated by alkylation and arylation similarly to nitrobenzenesulfonamides. The sulfonamides could withstand conditions that functionalize nitroarenes, such as reductions and vicarious nucleophilic substitution reactions.

Asymmetric Transfer Hydrogenation of Imines using Alcohol: Efficiency and Selectivity are Influenced by the Hydrogen Donor

The influence of the alcohol, as the hydrogen donor, on the efficiency and selectivity of the asymmetric transfer hydrogenation (ATH) of imines is reported for the first time. This discovery not only leads to a highly enantioselective access to N-aryl and N-alkyl amines, but also provides new insight into the mechanism of the ATH of imines. Both experimental and computational studies provide support for the reaction pathway involving an iridium alkoxide as the reducing species.

Graphene-supported NiPd alloy nanoparticles: A novel and highly efficient heterogeneous catalyst system for the reductive amination of aldehydes

A novel and highly efficient heterogeneous catalytic reductive amination of aldehydes is described. The recently developed graphene supported NiPd alloy nanoparticle (G-NiPd) catalyst using ammonia borane (AB) as a green, stable and safe hydrogen donor was used in a water/methanol mixture (v/v = 2/3) under ambient conditions. The catalytic system was successfully applied in the reductive amination of various substituted aldehydes with amines and the corresponding products were obtained in (up to) 99% yield in 6 h. The G-NiPd catalyst could be recycled up to five times without any significant loss in the product yield.

One-pot solvent-free reductive amination with a solid ammonium carbamate salt from CO2 and amine

Many amines are liquid and their handling is inconvenient compared with the corresponding solids. We transformed a liquid (S)-(-)-1-phenylethylamine 1 to the corresponding neutral solid form 2 by reacting with carbon dioxide. We performed reductive aminat

Asymmetric organocatalytic reduction of ketimines with catecholborane employing a N-triflyl phosphoramide Br?nsted acid as catalyst

The first asymmetric reduction of ketimines with catecholborane employing an enantiopure N-triflyl phosphoramide as the organocatalyst has been developed. Five mole % of the catalyst provides the corresponding secondary amines in very good to almost quantitative yields and good enantioselectivities up to 86:14 e.r. under mild reaction conditions.

Facile synthesis of (S,S)-1,2-diacylamides and (S,S)-1,2-diamines with C2-symmetry

A series of chiral vicinal tertiary diacylamides with C2- symmetry was synthesized from (S)-α-phenylethylamine, different aromatic aldehydes, and oxalyl chloride. The diacylamides obtained were then reduced to afford chiral vicinal diamines wit

S-SUBSTITUTED N-1- (HETERO)ARYL ALKYL-N - (HETERO)ARYL ALKYLYSOTHIOCARBAMIDES, METHOD FOR THE PRODUCTION THEREOF, PHYSIOLOGICALLY ACTIVE S-SUBSTITUTED N-1- (HETERO )ARYL ALKYL-N - (HETERO)ARYL ALKYLYSOTHIOCARBAMIDES,A PHARMACEUTICAL COMPOUND AND CURING METHOD

The invention relates to s-substituted N-1-[(hetero)aryl]alkyl-N-1-[(hetero)aryl]alkylysothio-carbamides and the physiologically active salts and bases thereof, embodied in the form of racemic mixtures (or stereoisomer mixture) or individual optical isomers. The specific physiological activity of said compounds makes it possible to use them in the form of molecular tools. Said invention also relates to Pharmaceutical compositions, containing said compounds and to a method for preventing and curing various diseases including neurodegenerative diseases as, for example Alzheimer's disease (AD). The pharmacological effect of said compounds is based on the combined cognitive-stimulating and neuroprotective action thereof, which is produced by acting on chemo-controlled calcium channels of neurone membranes, in particular the neurones regulated by glutamate receptors of the central neural system (CNS).

Application of monodentate secondary phosphine oxides, a new class of chiral ligands, in Ir(I)-catalyzed asymmetric imine hydrogenation

(Matrix presented) Secondary phosphine oxides were prepared from R 1PCl2 and R2MgBr, followed by hydrolysis. They were obtained in an enantiopure form by preparative chiral HPLC. These new monodentate ligands were tested in the iridium-catalyzed hydrogenation of imines at 25 bar. Enantioselectivities up to 76% were obtained at L/lr = 2. Addition of pyridine (Pyr/lr = 1:2) raised the ee to 83%. Using pyridine as an additive allowed reduction of the L/lr ratio to 1 without reduction of ee.