68285-25-6

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-(2-Fluorophenyl)ethylamine is used as a key building block in the synthesis of various pharmaceuticals. Its unique structure and properties make it an essential component in the development of new drugs with potential therapeutic applications.
Used in Organic Chemistry Research:
In the field of organic chemistry, (S)-1-(2-Fluorophenyl)ethylamine serves as a versatile intermediate for the synthesis of diverse chemical compounds. Its reactivity and functional groups allow for various chemical reactions, enabling the creation of complex organic molecules with specific properties and applications.
Used in Synthesis of Fluorinated Compounds:
Due to the presence of a fluorine atom, (S)-1-(2-Fluorophenyl)ethylamine is utilized in the synthesis of fluorinated compounds. Fluorination is an important modification in medicinal chemistry, as it can significantly impact the pharmacokinetic and pharmacodynamic properties of a molecule, leading to improved drug candidates.
Synthesis Methods:
(S)-1-(2-Fluorophenyl)ethylamine can be synthesized through several chemical reactions, including the reduction of the corresponding nitro compound or the reductive amination of the corresponding ketone. These methods provide efficient routes to obtain this valuable intermediate in organic chemistry.

InChI:InChI=1/C8H10FN/c1-6(10)7-4-2-3-5-8(7)9/h2-6H,10H2,1H3/t6-/m0/s1

Upstream product

• 130562-16-2 (αS,1'S)-N-(1-Phenylethyl)-2-fluoro-α-methylphenylmethylamine 
• 820208-98-8 C₈H₆O₄*C₁₆H₁₈FN 
• 1332832-14-0 (S)-1-(2-fluorophenyl)ethan-1-amine hydrochloride 
• 462-94-2 1,5-diaminopentane 
• 445-27-2 2'-Fluoroacetophenone 
• 124-20-9 N-(3-aminopropyl)-1,4-diaminobutane 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 185527-04-2 N-[1-(2-Fluoro-phenyl)-ethyl]-oxalamic acid octyl ester 
• 2836-82-0 (o-fluorophenyl)acetone 
• 109-73-9 N-butylamine 
• 445-26-1 1-(2-fluorophenyl)ethanol 
• 815-57-6 3-Methyl-2,4-pentanedione 
• 74788-44-6 1-(2-fluorophenyl)ethanamine 
• 87227-77-8 bishydrochloride salt of cis-1,4-diamino-but-2-ene 

Downstream Products

• 927175-31-3 [1-(2-fluoro-phenyl)-ethyl]-thiourea 
• 870709-92-5 2-[(S)-1-(2-fluorophenyl)ethylamino]-5-methylthiazol-4(5H)-one 
• 870713-26-1 2-((S)-1-(2-fluorophenyl)ethylamino)-5-(2-hydroxypropan-2-yl)-5-methylthiazol-4(5H)-one 
• 1332832-14-0 (S)-1-(2-fluorophenyl)ethan-1-amine hydrochloride 
• 1332827-96-9 (S)-2,2,2-trifluoro-N-(1-(2-(fluoro)phenyl)ethyl)acetamide 
• 445-27-2 2'-Fluoroacetophenone 

Relevant academic research and scientific papers

Application of “Smart” Amine Donors for Rapid Screening and Scale-Up of Transaminase-Mediated Biotransformations

The “smart” amine donors o-xylylenediamine and cadaverine were employed for the rapid screening of a large ketone library and subsequent preparative-scale synthesis of selected compounds using a commercially available amine transaminase, ATA256. The methodology enables both screening and preparative-scale biotransformations to be performed with a single enzyme and simplifies the generation of sp3-rich small-molecule libraries.

n-Butylamine as an alternative amine donor for the stereoselective biocatalytic transamination of ketones

Formal reductive amination has been a main focus of biocatalysis research in recent times. Among the enzymes able to perform this transformation, pyridoxal-5′-phosphate-dependent transaminases have shown the greatest promise in terms of extensive substrate scope and industrial application. Despite concerted research efforts in this area, there exist relatively few options regarding efficient amino donor co-substrates capable of allowing high conversion and atom efficiency with stable enzyme systems. Herein we describe the implementation of the recently described spuC gene, coding for a putrescine transaminase, exploiting its unusual amine donor tolerance to allow use of inexpensive and readily-available n-butylamine as an alternative to traditional methods. Via the integration of SpuC homologues with tandem co-product removal and cofactor regeneration enzymes, high conversion could be achieved with just 1.5 equivalents of the amine with products displaying excellent enantiopurity.

Biocatalytic transamination with near-stoichiometric inexpensive amine donors mediated by bifunctional mono- and di-amine transaminases

The discovery and characterisation of enzymes with both monoamine and diamine transaminase activity is reported, allowing conversion of a wide range of target ketone substrates with just a small excess of amine donor. The diamine co-substrates (putrescine, cadaverine or spermidine) are bio-derived and the enzyme system results in very little waste, making it a greener strategy for the production of valuable amine fine chemicals and pharmaceuticals.

Stereoselective amination of racemic sec-alcohols through sequential application of laccases and transaminases

A one-pot/two-step bienzymatic asymmetric amination of secondary alcohols is disclosed. The approach is based on a sequential strategy involving the use of a laccase/TEMPO catalytic system for the oxidation of alcohols into ketone intermediates, and their following transformation into optically enriched amines by using transaminases. Individual optimizations of the oxidation and biotransamination reactions have been carried out, studying later their applicability in a concurrent process. Therefore, 17 racemic (hetero) aromatic sec-alcohols with different substitutions in the aromatic ring have been converted into enantioenriched amines with good to excellent selectivities (90-99% ee) and conversion values (67-99%). The scalability of the process was also demonstrated when two different amine donors were used in the transamination step, such as isopropylamine and cis-2-buten-1,4-diamine. Satisfyingly, both sacrificial amine donors can shift the equilibrium toward the amine formation, leading to the corresponding isolated enantioenriched amines with good to excellent results.

Asymmetric catalysis of the carbonyl-amine condensation: Kinetic resolution of primary amines

A Br?nsted acid catalyzed kinetic resolution of primary amines is described that is based on the condensation between an amine and a carbonyl compound. 1,3-Diketones react with racemic α-branched amines to furnish the corresponding enantioenriched enaminone and recovered starting material. Good to excellent enantioselectivity was observed with both aromatic and aliphatic primary amines. This process represents the first small-molecule catalyzed kinetic resolution of aliphatic amines.

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.).

Chiral amine synthesis using ω-transaminases: An amine donor that displaces equilibria and enables high-throughput screening

The widespread application of ω-transaminases as biocatalysts for chiral amine synthesis has been hampered by fundamental challenges, including unfavorable equilibrium positions and product inhibition. Herein, an efficient process that allows reactions to proceed in high conversion in the absence of by-product removal using only one equivalent of a diamine donor (ortho-xylylenediamine) is reported. This operationally simple method is compatible with the most widely used (R)- and (S)-selective ω-TAs and is particularly suitable for the conversion of substrates with unfavorable equilibrium positions (e.g., 1-indanone). Significantly, spontaneous polymerization of the isoindole by-product generates colored derivatives, providing a high-throughput screening platform to identify desired ω-TA activity. ω-Transaminases (ω-TA) have been employed as biocatalysts in a simple and efficient process for the synthesis of chiral amines. A dual-function diamine donor (ortho-xylylenediamine) serves to displace challenging reaction equilibria towards product formation whilst generating intensely colored by-products, which have allowed the development of liquid-phase and colony-based assays.

Transaminases applied to the synthesis of high added-value enantiopure amines

Critical parameters affecting the stereoselective amination of (hetero)aromatic ketones using transaminases have been studied, such as temperature, pH, substrate concentration, cosolvent, and source and percentage of amino donor, to further optimize the production of enantiopure amines using both (S)- and (R)-selective biocatalysts from commercial suppliers. Interesting enantiopure amino building blocks have been obtained, overcoming some limitations of traditional chemical synthetic methods. Representative processes were scaled up, affording halogenated and heteroaromatic amines in enantiomerically pure form and good isolated yields.

Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: Applications toward the synthesis of calcimimetic agents

Highly enantiopure (1-aryl)- and (1-naphthyl)-1-ethylamines were synthesized by the borane-mediated reduction of single-isomeric (E)- and (Z)-O-benzyloxime ethers using the stable spiroborate ester derived from (S)-diphenyl valinol and ethylene glycol as the chiral catalyst. Primary (R)-arylethylamines were prepared by the reduction of pure (Z)-ethanone oxime ethers in up to 99% ee using 15% of catalyst. Two convenient and facile approaches to the synthesis of new and known calcimimetic analogues employing enantiopure (1-naphthalen-1-yl)ethylamine as chiral precursor are described.

N-BIPHENYLMETHYLINDOLE MODULATORS OF PPARG

The invention provides molecular entities that bind with high affinity to PPARG (PPAR3), inhibit kinase-mediated, e.g., cdk5-mediated, phosphorylation of PPARG, but do not exert an agonistic effect on PPARG. Compounds of the invention can be used for treatment of conditions in patients wherein PPARG plays a role, such as diabetes, insulin resistance, impaired glucose tolerance, pre-diabetes, hyperglycemia, hyperinsulinemia, obesity, or inflammation. In methods of treatment of these conditions using a compound of the invention, the compound can avoid producing side effects of significant weight gain, edema, impairment of bone growth or formation, or cardiac hypertrophy, or any combination thereof, in the patient receiving the compound. Methods of preparation of the compounds, bioassay methods for evaluating compounds of the invention as non-agonistic PPARG binding compounds, and pharmaceutical compositions are also provided.