57760-14-2

Upstream product

• 21869-55-6 3-methyl-4-phenylbutan-2-one 
• 108-24-7 acetic anhydride 
• 60-15-1 2-amino-1-phenylpropane 
• 141-78-6 ethyl acetate 
• 300-57-2 allylbenzene 
• 75-05-8 acetonitrile 
• 60-35-5 acetamide 
• 18793-46-9 (Z)-N-(1-Methyl-2phenylethenyl)ethanamide 
• 100835-72-1 N-benzyl-N-(1-methyl-2-phenylethyl)acetamide 
• 97305-91-4 (Z)-N-benzyl-N-(1-methyl-2-phenylvinyl)acetamide 
• 64-19-7 acetic acid 
• 1132-26-9 2-methyl-3-phenylalanine 
• 154-41-6 norephedrine hydrochloride 
• 18793-46-9 (E)-N-(1-Methyl-2-phenylethenyl)ethanamide 

Downstream Products

• 61630-03-3 N-[2-(4-acetyl-phenyl)-1-methyl-ethyl]-acetamide 
• 60-15-1 2-amino-1-phenylpropane 
• 42180-63-2 2-Amino-1-<4-sulfamoyl-phenyl>-propan 
• 1462-73-3 (S)-(+)-amphetamine hydrochloride 
• 41820-21-7 (-)-Amphetamine hydrochloride 
• 6309-84-8 4-(2-acetylamino-propyl)-benzoic acid 
• 33817-11-7 (S)-N-ethylamphetamine 
• 109441-25-0 5-[ethyl-((S)-1-methyl-2-phenyl-ethyl)-amino]-pentan-2-one 
• 101353-52-0 4-[ethyl-((S)-1-methyl-2-phenyl-ethyl)-amino]-butyronitrile 
• 51-64-9 dexamfetamine 

Relevant academic research and scientific papers

Transaminase-mediated synthesis of enantiopure drug-like 1-(3′,4′-disubstituted phenyl)propan-2-amines

Transaminases (TAs) offer an environmentally and economically attractive method for the direct synthesis of pharmaceutically relevant disubstituted 1-phenylpropan-2-amine derivatives starting from prochiral ketones. In this work, we report the application of immobilised whole-cell biocatalysts with (R)-transaminase activity for the synthesis of novel disubstituted 1-phenylpropan-2-amines. After optimisation of the asymmetric synthesis, the (R)-enantiomers could be produced with 88-89% conversion and >99% ee, while the (S)-enantiomers could be selectively obtained as the unreacted fraction of the corresponding racemic amines in kinetic resolution with >48% conversion and >95% ee. This journal is

ENVIRONMENTALLY-FRIENDLY HYDROAZIDATION OF OLEFINS

The present invention provides processes for the synthesis of organic azides, intermediates for the production thereof, and compositions related thereto.

Stereoselective Synthesis of 1-Arylpropan-2-amines from Allylbenzenes through a Wacker-Tsuji Oxidation-Biotransamination Sequential Process

Herein, a sequential and selective chemoenzymatic approach is described involving the metal-catalysed Wacker-Tsuji oxidation of allylbenzenes followed by the amine transaminase-catalysed biotransamination of the resulting 1-arylpropan-2-ones. Thus, a series of nine optically active 1-arylpropan-2-amines were obtained with good to very high conversions (74–92%) and excellent selectivities (>99% enantiomeric excess) in aqueous medium. The Wacker-Tsuji reaction has been exhaustively optimised searching for compatible conditions with the biotransamination experiments, using palladium(II) complexes as catalysts and iron(III) salts as terminal oxidants in aqueous media. The compatibility of palladium/iron systems for the chemical oxidation with commercially available and made in house amine transaminases was analysed, finding ideal conditions for the development of a general and stereoselective cascade sequence. Depending on the selectivity displayed by selected amine transaminase, it was possible to produce both 1-arylpropan-2-amines enantiomers under mild reaction conditions, compounds that present therapeutic properties or can be employed as synthetic intermediates of chiral drugs from the amphetamine family. (Figure presented.).

Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins

We herein report a direct intermolecular anti-Markovnikov hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation procedures, and thereby provides a valuable tool for azido-group labeling in organic synthesis and chemical biology studies.

But-2-ene-1,4-diamine and But-2-ene-1,4-diol as Donors for Thermodynamically Favored Transaminase- and Alcohol Dehydrogenase-Catalyzed Processes

Both cis- and trans-but-2-ene-1,4-diamines have been prepared and efficiently applied as sacrificial cosubstrates in enzymatic transamination reactions. The best results were obtained with the cis-diamine. The thermodynamic equilibrium of the stereoselective transamination process is shifted to the amine formation due to tautomerization of 5H-pyrrole into 1H-pyrrole, achieving high conversions (78–99%) and enantiomeric excess (up to >99%) by using a small excess of the amine donor. Furthermore, when the reaction proceeded, a strong coloration was observed due to polymerization of 1H-pyrrole. A structurally related compound, cis-but-2-ene-1,4-diol, has been utilized as cosubstrate in different alcohol dehydrogenase (ADH)-mediated bioreductions. In this case, high conversions (91–99%) were observed due to a lactonization process. Both strategies are convenient from both synthetic and atom economy points of view in the production of valuable optically active products. (Figure presented.).

Enantioselective hydrogenation of α,β-disubstituted nitroalkenes

The first highly chemo- and enantioselective hydrogenation of α,β-disubstituted nitroalkenes was accomplished with rhodium/JosiPhos-J2 as a catalyst, with the yield and enantioselectivity of up to 95% and 94%, respectively. The α-chiral nitroalkanes will provide an entry to valuable chiral amphetamines which are otherwise not so easily accessed. This journal is the Partner Organisations 2014.

Enantioselective hydrogenation of (Z)- and (E)-β-arylenamides catalyzed by rhodium complexes of monodentate chiral spiro phosphorous ligands: A new access to chiral β-arylisopropylamines

A highly enantioselective rhodium-catalyzed hydrogenation of both (Z)- and (E)-β-arylenamides was developed by using monodentate chiral spiro phosphite and phosphine ligands, respectively. The hydrogenation reaction provides an efficient access to optically active β-arylisopropylamines, important building blocks for the synthesis of biologically active compounds.

New synthetic strategy for high-enantiopurity N-protected α-amino ketones and their derivatives by asymmetric hydrogenation

Asymmetric hydrogenation of α-dehydroamino ketones catalyzed by a rhodium-chiral phosphorus ligand complex (up to 99% ee, 1000 TON), represents an efficient approach to chiral α-amino ketones. The reduction of α-amino ketones catalyzed by palladium on carbon (Pd/C) leads to amphetamine precursors with quantitative yield and no significant enantioselectivity loss.

METHOD FOR MAKING PHARMACEUTICAL COMPOUNDS

A method of making a phenylethylamine of formula B: wherein R2, R3, R4, R5, R6, Rα, Rβ and Rn are each independently selected from hydrogen, alkyl, acyl, aryl, amido, amino acids, sugars and nucleotides. The method includes the reduction of a compound of formula A in the absence of base: wherein R2, R3, R4, R5, R6, Rα, Rβ and Rn are as defined above.

Efficient synthesis of chiral β-arylisopropylamines by using catalytic asymmetric hydrogenation

(Chemical Equation Presented) Direct condensation of β-arylketones with acetamide afforded both Z and E enamides. The Z-configured substrates underwent hydrogenation with excellent enantioselectivity by using the Rh/tang-phos catalytic system (see scheme; tangphos = 1,1′-di-tert-butyl- [2,2′]-diphospholanyl). The product β-arylisopropylamines are important precursors to several drugs.