167421-83-2

Usage

Chemical Properties

Off-White Solid

Uses

Protected (R)-Amphetamine.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 156-34-3 l-amphetamine 
• 63-91-2 L-phenylalanine 
• 114352-01-1 (R)-amphetamine D-tartaric salt 
• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 863482-65-9 1-((R)-2-azidopropyl)benzene 
• 122-78-1 phenylacetaldehyde 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 591-51-5 phenyllithium 
• 454248-53-4 (R)-4-methyl-2,2-dioxo-1,2,3-oxathiazolidine-3-carboxylic acid tert butyl ester 
• 79069-13-9 (R)-2-tertbutoxycarbonylamino-1-propanol 
• 126301-19-7 (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl methanesulfonate 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 3182-95-4 L-Phenylalaninol 

Downstream Products

• 41820-21-7 (-)-Amphetamine hydrochloride 
• 156-34-3 l-amphetamine 
• 33817-09-3 (R)-2-methylamino-1-phenylpropane 
• 2323-36-6 SELEGILINE 
• 1254494-15-9 (R)-N-d3-methyl-1-phenylpropan-2-amine 

Relevant academic research and scientific papers

Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines

α-Chiral alkyl primary amines are virtually universal synthetic precursors for all other α-chiral N-containing compounds ubiquitous in biological, pharmaceutical, and material sciences. The enantioselective amination of common alkyl halides with ammonia is appealing for potential rapid access to α-chiral primary amines, but has hitherto remained rare due to the multifaceted difficulties in using ammonia and the underdeveloped C(sp3)-N coupling. Here we demonstrate sulfoximines as excellent ammonia surrogates for enantioconvergent radical C-N coupling with diverse racemic secondary alkyl halides (>60 examples) by copper catalysis under mild thermal conditions. The reaction efficiently provides highly enantioenrichedN-alkyl sulfoximines (up to 99% yield and >99% ee) featuring secondary benzyl, propargyl, α-carbonyl alkyl, and α-cyano alkyl stereocenters. In addition, we have converted the masked α-chiral primary amines thus obtained to various synthetic building blocks, ligands, and drugs possessing α-chiral N-functionalities, such as carbamate, carboxylamide, secondary and tertiary amine, and oxazoline, with commonly seen α-substitution patterns. These results shine light on the potential of enantioconvergent radical cross-coupling as a general chiral carbon-heteroatom formation strategy.

PHENETHYL SUBSTITUTED IMIDAZO[4,5-C]QUINOLINE COMPOUNDS WITH AN N-1 BRANCHED GROUP

Imidazo[4,5-c]quinoline compounds having a substituent that is attached at the N-1 position by a branched group, single enantiomers of the compounds, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed.

Hydrodehalogenation of alkyl iodides with base-mediated hydrogenation and catalytic transfer hydrogenation: Application to the asymmetric synthesis of N-protected α-methylamines

We report a very mild synthesis of N-protected α-methylamines from the corresponding amino acids. Carboxyl groups of amino acids are reduced to iodomethyl groups via hydroxymethyl intermediates. Reductive deiodination to methyl groups is achieved by hydrogenation or catalytic transfer hydrogenation under alkaline conditions. Basic hydrodehalogenation is selective for the iodomethyl group over hydrogenolysis-labile protecting groups, such as benzyloxycarbonyl, benzyl ester, benzyl ether, and 9-fluorenyloxymethyl, thus allowing the conversion of virtually any protected amino acid into the corresponding N-protected α-methylamine.

Synthesis of (R)-selegiline via hydrolytic kinetic resolution

A short and enantioselective formal synthesis of (R)-selegiline has been achieved using Jacobsen's hydrolytic kinetic resolution (HKR) of phenyl propylene oxide.

Ring opening of cyclic sulfamidates with bromophenyl metal reagents: Complementarity of sulfamidates and aziridines

Bromophenyl magnesium reagents generated via a Knochel type magnesium-halogen exchange of aryl iodides undergo regioselective ring opening of cyclic primary and secondary N-Boc sulfamidates in good to excellent yields. With secondary sulfamidates the reaction proceeds with clean inversion of the stereochemistry. This protocol complements the ring opening of aziridines with bromophenyl metal reagents and extends its scope to secondary substrates.

CHEMICAL COMPOUNDS

The invention is directed to 6-(4-pyι?midinyl)-1 H-indazole derivatives. Specifically, the invention is directed to compounds according to Formula (I) wherein R1 - R4 are defined herein. The compounds of the invention are inhibitors of PDK1 and can be useful in the treatment of immune and metabolic diseases and disorders characterized by constitutively activated ACG kinases such as cancer and more specifically cancers of the breast, colon, and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PDK1 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

PROP-2-YN-1-AMINE INHIBITORS OF MONOAMINE OXIDASE TYPE B

The present invention relates to new prop-2-yn-1-amine inhibitors of monoamine oxidase type B activity, pharmaceutical compositions thereof, and methods of use thereof.

N-Acyl glycinates as acyl donors in serine protease-catalyzed kinetic resolution of amines. Improvement of selectivity and reaction rate

Enzymatic kinetic resolution of aliphatic and benzylic amines leading to (S)-amides was achieved by using alkaline protease as the catalyst and N-octanoyl glycine trifluoroethyl ester as the acyl donor; enantioselectivity ranged between 4 to 244, while reaction times were dramatically shortened and ranged between 15 min to 6 h. The 2008 Royal Society of Chemistry.

An organo-catalytic approach to the enantioselective synthesis of (R)-selegiline

An efficient enantioselective synthesis of (R)-selegiline has been achieved by two routes, via proline-catalyzed α-aminooxylation as well as α-amination of phenylpropanaldehyde as the key step.

Correlation between the6Li,15N coupling constant and the coordination number at lithium

The 6Li,15N coupling constants of lithium amide dimers and their mixed complexes with n-butyllithium, formed from five different chiral amines derived from (S)-[15N]phenylalanine, were determined in diethyl ether (Et2O), tetrahydrofuran (THF) and toluene. Results of NMR spectroscopy studies of these complexes show a clear difference in 6Li, 15N coupling constants between di-, tri- and tetracoordinated lithium atoms. The lithium amide dimers with a chelating ether group exhibit 6Li,15N coupling constants of ～3.8 and ～5.5 Hz for the tetracoordinated and tricoordinated lithium atoms, respectively. The lithium amide dimers with a chelating thioether group show distinctly larger 6Li,15N coupling constants of ～4.4 Hz for the tetracoordinated lithium atoms, and the tricoordinated lithium atoms have smaller 6Li, 15N coupling constants, ～4.9 Hz, than their ether analogues. In diethyl ether and tetrahydrofuran, mixed dimeric complexes between the lithium amides and n-butyllithium are formed. The tetracoordinated lithium atoms of these complexes have 6Li, 15N coupling constants of ～4.0 Hz, and the 6Li, 15N coupling constants of the tricoordinated lithium atoms differ somewhat, depending on whether the chelating group is an ether or a thioether; ～5.1 and ～4.6 Hz, respectively. In toluene, mixed trimeric complexes are formed from two lithium amide moieties and one n-butyl-lithium. In these trimers, two lithium atoms are tricoordinated with 6Li,15N coupling constants of ～4.6 Hz and one lithium is dicoordinated with 6Li,15N coupling constants of ～6.5 Hz.