115914-08-4

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-N-ALLYL-ALPHA-METHYLBENZYLAMINE& is utilized as a key intermediate in the development and synthesis of various pharmaceutical products. Its role in creating drugs that treat allergies and respiratory problems is particularly noteworthy, given the prevalence of these health concerns worldwide.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-(-)-N-ALLYL-ALPHA-METHYLBENZYLAMINE& serves as a crucial component in the formulation of products designed to enhance agricultural productivity and protect crops from pests and diseases.
Used in Fine Chemicals Production:
(S)-(-)-N-ALLYL-ALPHA-METHYLBENZYLAMINE& is also employed in the production of fine chemicals, which are specialty chemicals used in various applications, including fragrances, dyes, and coatings. Its unique properties make it an indispensable component in the creation of these high-value products.
Organic Synthesis:
(S)-(-)-N-ALLYL-ALPHA-METHYLBENZYLAMINE& is a building block in organic synthesis, where it contributes to the formation of complex organic compounds that have a wide range of applications across different industries. Its versatility and reactivity make it a valuable asset in the field of chemical research and development.

InChI:InChI=1/C11H15N/c1-3-9-12-10(2)11-7-5-4-6-8-11/h3-8,10,12H,1,9H2,2H3/t10-/m1/s1

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 106-95-6 allyl bromide 
• 107-05-1 3-chloroprop-1-ene 
• 556-56-9 allyl iodid 
• 35021-93-3 N-(1-phenylethylidene)prop-2-en-1-amine 
• 98-85-1 1-Phenylethanol 
• 98-86-2 acetophenone 
• 107-11-9 1-amino-2-propene 
• 336628-49-0 1,3-dichloro-2-propyl (S)-N-(1-phenylethyl)carbamate 
• 336628-48-9 1,3-dibromo-2-propyl (S)-N-(1-phenylethyl)carbamate 
• 14649-03-7 (S)-phenylethyl isocyanate 
• 336628-51-4 (5R,1'S)-5-bromomethyl-3-(1'-phenylethyl)-2-oxazolidinone 
• 336628-52-5 (5R,1'S)-5-chloromethyl-3-(1'-phenylethyl)-2-oxazolidinone 
• 160865-32-7 (S)-N-allyl-N-(1-phenylethyl)prop-2-en-1-amine 

Downstream Products

• 138202-74-1 2,3-Dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid allyl-((S)-1-phenyl-ethyl)-amide 
• 164660-15-5 (R)-3-[Allyl-((S)-1-phenyl-ethyl)-amino]-3-phenyl-propionic acid tert-butyl ester 
• 175469-08-6 N-benzyl,N-(5,5-dimethyl-3-oxo-cyclohex-1-enyl)-2-aminoacetamide 
• 186299-49-0 (S)-N-allyl-N-(1-phenylethyl)methoxycarbonylacetamide 
• 186299-50-3 (S)-N-(1-pphenyleth-1-yl)-N-(1-prop-2-enyl)-3-oxobutanamide 
• 468071-31-0 (3S,5E,αS)-methyl 3-(N-allyl-N-α-methylbenzylamino)-hept-5-enoate 
• 811449-04-4 (S)-N-allyl-2-bromo-N-(1-phenyl-ethyl)acetamide 
• 113420-83-0 (1'S^*,5R^*)-3-(1'-phenyleth-1'yl)-5-(iodomethyl)oxazolidin-2-one 
• 113420-77-2 (1'S^*,5S^*)-3-(1'-phenyleth-1'yl)-5-(iodomethyl)oxazolidin-2-one 

Relevant academic research and scientific papers

Visible Light-Mediated Synthesis of Enantiopure γ-Cyclobutane Amino and 3-(Aminomethyl)-5-phenylpentanoic Acids

A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-azabicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into γ-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobutane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant, is described.

Visible Light-Mediated Synthesis of Enantiopure g-Cyclobutane Amino and 3-(Aminomethyl)-5-phenylpentanoic Acids

A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-aza-bicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into g-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobu-tane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant is described.

Metal-free, mild, nonepimerizing, chemo- and enantio- or diastereoselective N-alkylation of amines by alcohols via oxidation/imine-iminium formation/reductive amination: A pragmatic synthesis of octahydropyrazinopyridoindoles and higher ring analogues

A mild step and atom-economical nonepimerizing chemo- and enantioselective N-alkylating procedure has been developed via oxidation/imine-iminium formation/reduction cascade using TEMPO-BAIB-HEH-Bronsted acid catalysis in DMPU as solvent and a stoichiometric amount of amine. The optimized conditions were further extended for the nonenzymatic kinetic resolution of the chiral amine thus formed under nonenzymatic in situ hydrogen-transfer conditions using VAPOL-derived phosphoric acid (VAPOL-PA) as the Bronsted acid catalyst. The enantioselective cascade of the presented reaction was successfully utilized in the synthesis of octahydropyrazinopyridoindole and its higher ring analogues.

1,1′-Binaphthyldiamine-based lewis bases as readily available and efficient grganocatalysts for the reduction of N-Aryl and N-Alkyl ketimines

The development of simple, low-cost, efficient, and sustainable routes to enantiomerically pure amines is a topic of extraordinary interest, specially in view of future industrial applications. In this context, we wish to report a chemical and stereochemical efficient synthesis of chiral amines through the Lewis base activated trichlorosilane reduction of ketimines. An organocatalyst, easily prepared in a single step through the condensation of picolinic acid and commercially available 1,1′-binaphthyldiamine, is the key element of this metal-free methodology, that allowed the synthesis of chiral secondary and primary amines in high yields and stereose-lectivity. Noteworthy, such catalysts are able to promote the reduction of N-alkyl ketimines, often in quantitative yield and up to 87% enantioselectivity; it: is worth mentioning that for such transformations only one other organocatalytic system has been reported so far.

Stereoselective 5-exo-trig radical cyclization in the enantioselective synthesis of Pregabalin

A practical stereoselective 5-exo-trig radical cyclization procedure was developed in order to prepare enantiomerically pure GABA derivative precursors (4-alkyl-pyrrolidin-2-ones). This procedure allows much more rapid access to optically pure GABA derivatives, such as the powerful antiepileptic agent (S)-(+)-3-aminomethyl-5-methylhexanoic acid (Pregabaline).

Synthesis of enantiomerically pure (+)- and (-)-protected 5-aminomethyl-1,3-oxazolidin-2-one derivatives from allylamine and carbon dioxide

The stereoselective synthesis of enantiomerically pure (5R)- and (5S)-aminomethyl-oxazolidinones with different protecting groups have been carried out from an allyl amine as the source of the carbon backbone. The key reaction is the high yield iodiocyclization of enantiomerically pure allylphenethyl amine in the presence of carbon dioxide.

The 5-exo-trig radical cyclization reaction under reductive and oxidative conditions in the synthesis of optically pure GABA derivatives

Free radical precursors 4a and 4b were synthesized and treated under reductive or oxidative conditions to obtain the corresponding optically pure pyrrolidinones 5-8, which were subsequently transformed into corresponding optically pure GABA derivatives 9-11. When reductive radical conditions (4a→7 and 8) were used, a Ph1-5 migration product 14 was obtained; presumably depending upon the specific conformation of the rotamer precursor and also 14 was found to be a kinetic product.

Pilot Plant Preparation of an αvβ3 Integrin Antagonist. Part 1. Process Research and Development of a (S)-β-Amino Acid Ester Intermediate: Synthesis via a Scalable, Diastereoselective Imino-Reformatsky Reaction

Described are four process research investigations directed toward discerning a scalable, enantioselective method for preparing (S)-β-amino acid ester 3, a key intermediate to the αvβ3 integrin antagonist 1. Reported are an asymmetric Michael reaction approach, attempts to enantioselectively hydrogenate an enamine, resolution of (±)-3 via diastereomeric salt formation, and a synthetic route employing a novel, diastereoselective imino-Reformatsky reaction. This last research initiative proved successful and was employed as the enabling route to initial API supply. Process development of this enabling chemistry is reported. The technical issues researched and optimized were (1) the necessity of employing MEM-protection for high yield and diastereoselectivity in the imino-Reformatsky reaction, (2) the reaction kinetics of MEM chloride hydrolysis and the application of these data to an on-scale quench procedure, (3) the efficient formation of the (S)-phenylglycinol imine 15 in NMP and a dehydration of this product solution on-scale, employing molecular sieves, (4) a calorimetric study of the Reformatsky reaction and the application of these data, (5) the replacement of Pb(OAc)4 with NaIO4 and the use of methylamine to sequester competing oxazolidine formation, and (6) further development of the isolation and purification protocol for the ethyl ester, p-TsOH salt of (S)-3. The results and challenges associated with two campaigns in which the potential commercial process was practiced are discussed.

A three-step synthesis of optically active 5-halomethyl-2-oxazolidinones; asymmetric desymmetrization of prochiral 1,3-dihalo-2-propyl carbamates

Optically active 5-bromomethyl-2-oxazolidinones (2a and 3a) and 5-chloromethyl-2-oxazolidinones (2b and 3b) were readily prepared from prochiral 1,3-dibromo-2-propanol (7a) and 1,3-dichloro-2-propanol (7b) by a three-step sequence involving formation of carbamates (6a-c) followed by asymmetric desymmetrization (up to 50% de) and debenzylation by anisole-methanesulfonic acid system.

Diastereocontrolled synthesis of pyrrolidines by nickel promoted tandem cyclization-quenching of aminobromodienes

The nickel promoted tandem cyclization-quenching of tethered aminobromodienes has been extended to the synthesis of 2,3,4-trisubstituted pyrrolidines. By a judicious choice of substituents on the starting aminohalodiene, the diastereoselectivity of the process can be efficiently controlled. When a chiral auxiliary on the nitrogen atom is used, enantiomerically enriched pyrrolidines can be obtained after removal of the auxiliary.