46084-23-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is used as a stimulant for its ability to increase heart rate and blood pressure, making it useful in treating conditions that require stimulation of the central nervous system.
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is used as an appetite suppressant due to its ability to reduce appetite, which can be beneficial for weight management and obesity treatment.
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is used as a decongestant for its ability to relieve nasal congestion by constricting blood vessels in the nasal passages.
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is used as a bronchodilator for its ability to widen the airways, which can be helpful in treating conditions like asthma and other respiratory disorders.
Used in Synthesis of Pharmaceuticals:
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is used as a precursor in the synthesis of various pharmaceuticals, taking advantage of its chemical properties to create a range of different medications.
Used in Illicit Drug Manufacturing:
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol has also been used as a precursor for the illicit manufacturing of drugs, although this use is illegal and highly regulated due to the potential for abuse and adverse effects.
Regulation and Prescription Requirement:
Due to its potential for abuse and adverse effects, (R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is regulated in many countries and requires a prescription for medical use. This ensures that the compound is used responsibly and under the supervision of a healthcare professional.

Upstream product

• 97070-73-0 (R)-(+)-α-Hydroxy-4-methoxybenzeneacetonitrile 
• 341513-45-9 (R)-β-azido-α-(4-methoxyphenyl)ethanol 
• 3883-94-1 2-amino-4'-methoxyacetophenone hydrochloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 3755-89-3 N-(2-(4-methoxyphenyl)-2-oxoethyl)acetamide 
• 1287753-52-9 (E)-2-(4-methoxyphenyl)-2-oxoacetaldehyde O-benzyl oxime 
• 67867-35-0 (E)-2-(4-methoxyphenyl)-2-oxoacetaldehyde oxime 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 637-69-4 4-Methoxystyrene 
• 13603-63-9 (R)-1-(4-methoxyphenyl)ethane-1,2-diol 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 6595-28-4 2-azido-1-(4-methoxyphenyl)ethan-1-one 
• 675579-60-9 (2R,6S)-2-[(R)-1-(4-Methoxy-phenyl)-2-nitro-ethoxy]-6-methyl-tetrahydro-pyran 
• 604808-45-9 (S)-2-(diethylphosphoryloxy)-2-(4-methoxyphenyl)acetonitrile 

Downstream Products

• 37791-56-3 (R)-(-)-N-(2-hydroxy-2-(4-methoxyphenyl)ethyl)benzamide 
• 1033599-12-0 C₂₇H₂₉NO₆ 
• 1033599-29-9 C₂₇H₂₉NO₆ 

Relevant academic research and scientific papers

Enantioselective Aminohydroxylation of Styrenyl Olefins Catalyzed by an Engineered Hemoprotein

Chiral 1,2-amino alcohols are widely represented in biologically active compounds from neurotransmitters to antivirals. While many synthetic methods have been developed for accessing amino alcohols, the direct aminohydroxylation of alkenes to unprotected, enantioenriched amino alcohols remains a challenge. Using directed evolution, we have engineered a hemoprotein biocatalyst based on a thermostable cytochrome c that directly transforms alkenes to amino alcohols with high enantioselectivity (up to 2500 TTN and 90 % ee) under anaerobic conditions with O-pivaloylhydroxylamine as an aminating reagent. The reaction is proposed to proceed via a reactive iron-nitrogen species generated in the enzyme active site, enabling tuning of the catalyst's activity and selectivity by protein engineering.

Norepinephrine alkaloids as antiplasmodial agents: Synthesis of syncarpamide and insight into the structure-activity relationships of its analogues as antiplasmodial agents

Syncarpamide 1, a norepinephrine alkaloid isolated from the leaves of Zanthoxylum syncarpum (Rutaceae) exhibited promising antiplasmodial activities against Plasmodium falciparum with reported IC50 values of 2.04 μM (D6 clone), 3.06 μM (W2 clone) and observed by us 3.90 μM (3D7 clone) and 2.56 μM (K1 clone). In continuation of our work on naturally occurring antimalarial compounds, synthesis of syncarpamide 1 and its enantiomer, (R)-2 using Sharpless asymmetric dihydroxylation as a key step has been accomplished. In order to study structure-activity-relationship (SAR) in detail, a library of 55 compounds (3–57), which are analogues/homologues of syncarpamide 1 were synthesized by varying the substituents on the aromatic ring, by changing the stereocentre at the C-7 and/or by varying the acid groups in the ester and/or amide side chain based on the natural product lead molecule and further assayed in vitro against 3D7 and K1 strains of P. falciparum to evaluate their antiplasmodial activities. In order to study the effect of position of functional groups on antiplasmodial activity profile, a regioisomer (S)-58 of syncarpamide 1 was synthesized however, it turned out to be inactive against both the strains. Two compounds, (S)-41 and its enantiomer, (R)-42 having 3,4,5-trimethoxy cinnamoyl groups as side chains showed better antiplasmodial activity with IC50 values of 3.16, 2.28 μM (3D7) and 1.78, 2.07 μM (K1), respectively than the natural product, syncarpamide 1. Three compounds (S)-13, (S)-17, (S)-21 exhibited antiplasmodial activities with IC50 values of 6.39, 6.82, 6.41 μM against 3D7 strain, 4.27, 7.26, 2.71 μM against K1 strain and with CC50 values of 147.72, 153.0, >200 μM respectively. The in vitro antiplasmodial activity data of synthesized library suggests that the electron density and possibility of resonance in both the ester and amide side chains increases the antiplasmodial activity as compared to the parent natural product 1. The natural product syncarpamide 1 and four analogues/homologues out of the synthesized library of 55, (S)-41, (R)-42, (S)-55 and (S)-57 were assayed in vivo assay against chloroquine-resistant P. yoelii (N-67) strain of Plasmodium. However, none of the five molecules, 1, (S)-41, (R)-42, (S)-55 and (S)-57 exhibited any promising in vivo antimalarial activity against P. yoelii (N-67) strain. Compounds 4, 6, 7 and 11 showed high cytotoxicities with CC50 values of 5.87, 5.08, 6.44 and 14.04 μM, respectively. Compound 6 was found to be the most cytotoxic as compared to the standard drug, podophyllotoxin whereas compounds 4 and 7 showed comparable cytotoxicities to podophyllotoxin.

A Green approach towards the synthesis of chiral alcohols using functionalized alginate immobilized Saccharomyces cerevisiae cells

The stereochemistry of the drug molecule is gaining greater therapeutic importance and thus much attention was drawn in synthesis of chiral compounds by the pharmaceutical industry. In this study Saccharomyces cerevisiae cells immobilized on functionalize

Enantioselective Henry and aza-Henry reaction in the synthesis of (R)-tembamide using efficient, recyclable polymeric CuII complexes as catalyst

Chiral copper(II) polymeric [H4]salen (salen=bis[(salicylidene) ethylenediaminato]) complexes CuII-1-3 were generated in situ and used as efficient catalysts in the asymmetric Henry and aza-Henry reaction of various aromatic and alip

One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.

Asymmetric reduction of α-keto aldoxime o -ethers

The catalytic asymmetric reduction of -keto aldoxime O-methyl, O-benzyl, and O-trityl ethers, derived from substituted acetophenones, with borane/oxazaborolidines, by transfer hydrogenation, and with yeast, was studied. The reduction with borane/oxazaborolidines produced the corresponding -hydroxy oxime ethers, -hydroxy hydroxylamine ethers, and -amino alcohols in 39-78% yields and up to 77% ee. The carbonyl group was selectively reduced by transfer hydrogenation with formic acid-triethylamine catalyzed by RhCl[(R,R)-TsDPEN](Ce, and also with yeast, producing -hydroxy oxime ethers, up to 75% ee and 93% ee, respectively. Georg Thieme Verlag Stuttgart New York.

Asymmetric hydrogenation of α-primary and secondary amino ketones: Efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine

Two ss-receptor agonists (-)-denopamine and (-)-arbutamine were prepared in good yields and enantioselectivities by asymmetric hydrogenation of unprotected amino ketones for the first time by using Rh catalysts bearing electron-donating phosphine ligands. A series of α-primary and secondary amino ketones were synthesized and hydrogenated to produce various 1,2-amino alcohols in good yields and with good enantioselectivies. This Rh electron-donating phosphine-catalyzed asymmetric hyderogenation repI resents one of the most promising and convenient approaches towards the asymmetric synthesis of chiral amino alcohols.

Asymmetric transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives: synthesis of (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine

Catalytic transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives leads to efficient synthesis of β-adrenergic agonists, (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine.

Binolam-AlCl: A two-centre catalyst for the synthesis of enantioenriched cyanohydrin O-phosphates

The enantioselective synthesis of cyanohydrin O-phosphates by using in situ generated bifunctional catalysts (R)- or (S)-3,3′-bis(diethylaminomethyl) -1, 1′-binaphthol-aluminium chloride (binolam-AlCl) is reported. The reaction, which can be described as an overall cyano-O-phosphorylation of aldehydes, has a wide scope and applicability. Evidence is also provided, including ab initio and DFT calculations, in support of supported by the Lewis acid/Bronsted base (LABB) dual role of the catalyst in inducing first the key enantioselective hydrocyanation, which is then followed by O-phosphorylation. A brief screening of the synthetic usefulness of the resulting cyanohydrin O-phosphates unveiles some interesting applications. Among them, chemoselective hydrolysis, reduction and palladium-catalysed nucleophilic allyl substitution, thereby leading to enantiomerically enriched α-O-phosphorylated α-hydroxy esters, β-amino alcohols and γ-cyanoallyl alcohols, respectively. Naturally occurring (-)-tembamide and (-)-aegeline are synthesised accordingly.

Short asymmetric syntheses of bioactive β-aryl ethanolamine derivatives via the highly diastereoselective delta lactol oxy-Michael addition

Short, stereoselective and efficient total syntheses of the bioactive β-aryl ethanolamine derivatives (R)-tembamide, (R)-aegeline and (R)-pronethalol have been achieved using the highly diastereoselective oxy-Michael addition of 'naked' delta lactol anion