100929-33-7

Basic information

• Product Name: (R)-b-AMino-4-Methoxy-benzeneethanol
• Synonyms: (R)-b-AMino-4-Methoxy-benzeneethanol;(2R)-2-AMINO-2-(4-METHOXYPHENYL)ETHAN-1-OL;(R)-2-Amino-2-(4-methoxyphenyl)ethanol;(R)-2-amino-2-(4-methoxyphenyl)ethan-1-ol;(R)-2-amino-2-(4-methoxyphenyl)-1-ethanol
• CAS NO: 100929-33-7
• Molecular Formula: C₉H₁₃NO₂
• Molecular Weight: 167.20502
• Mol File: 100929-33-7.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: (R)-b-AMino-4-Methoxy-benzeneethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-b-AMino-4-Methoxy-benzeneethanol(100929-33-7)
• EPA Substance Registry System: (R)-b-AMino-4-Methoxy-benzeneethanol(100929-33-7)

Safety Data

• Hazardous Substances Data: 100929-33-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(R)-b-Amino-4-Methoxy-benzeneethanol is used as a building block for the synthesis of various pharmaceutical compounds due to its versatile functional groups and unique structure. Its chiral nature allows for the development of enantiomer-specific drugs, which can have different pharmacological effects and reduce potential side effects.
Used in Organic Synthesis:
In the field of organic synthesis, (R)-b-Amino-4-Methoxy-benzeneethanol serves as a valuable intermediate for the creation of complex molecules and compounds. Its functional groups can be manipulated to form a wide range of products, making it a useful tool for chemists in designing and synthesizing novel molecules.
Used as a Chiral Resolving Agent:
(R)-b-Amino-4-Methoxy-benzeneethanol has the potential to be used as a chiral resolving agent in the separation and purification of enantiomers. This application is particularly relevant in the pharmaceutical industry, where the development of pure enantiomers is crucial for ensuring the safety and efficacy of drugs.
Used in Drug Development:
(R)-b-AMino-4-Methoxy-benzeneethanol's potential applications in drug development stem from its ability to serve as a building block for the synthesis of pharmaceutical compounds. Its unique structure and functional groups can be leveraged to create new drugs with improved properties, such as increased potency, selectivity, and reduced side effects.

Upstream product

• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 159848-74-5 1,1-dimethylethyl (R)-N-[2-hydroxy-1-(4-methoxyphenyl)-ethyl]carbamate 
• 101128-44-3 isopropyl 2-(4-methoxyphenyl)-2-oxoacetate 
• 19922-83-9 (S)-1-bromo-2-hydroxy-2-(p-methoxyphenyl)ethane 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 213136-30-2 (R)-2-(((benzyloxy)carbonyl)amino)-2-(4-hydroxyphenyl)acetate methyl ester 
• 57591-61-4 methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate hydrochloride 
• 199392-93-3 Benzyl (R)-2-hydroxy-1-(4-methoxyphenyl)ethylcarbamate 
• 637-69-4 4-Methoxystyrene 
• 22818-40-2 D-4-hydroxyphenylglycine 
• 1268345-15-8 (R)-2-[(methoxycarbonyl)amino]-2-(4-methoxyphenyl)-1-ethanol 
• 1268345-14-7 methyl (R)-2-[(methoxycarbonyl)amino]-2-(4-methoxyphenyl) acetate 
• 77568-43-5 (R)-2-(4-hydroxyphenyl)-2-[(methoxycarbonyl)amino]acetic acid 
• 78307-39-8 methyl 4-methoxyphenyl-D-phenylglycinate 

Downstream Products

• 1383845-24-6 O-TMS-p-methoxyphenylglycinol 
• 209530-22-3 (R)-2-(1,3-Dihydro-isoindol-2-yl)-2-(4-methoxy-phenyl)-ethanol 
• 1268344-84-8 1-[(R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 1268344-86-0 1-[(R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-5-D-1H-pyrrol-2(5H)-one 
• 1268344-87-1 1-[(R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-5-methyl-1H-pyrrol-2(5H)-one 
• 1268344-88-2 1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-5-methyl-1H-pyrrol-2(5H)-one 
• 1268344-89-3 5-ethyl-1-[(R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 1268344-90-6 5-ethyl-1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 1268344-91-7 (R)-5-ethyl-1-[(R)-1-(3-ethyl-4-methoxyphenyl)-2-hydroxyethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 1268344-92-8 5-butyl-1-[(R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 1268344-93-9 5-butyl-1-[(R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 1268344-94-0 (R)-5-butyl-1-[(R)-1-(3-butyl-4-methoxyphenyl)-2-hydroxyethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 1268344-95-1 5-hexyl-1-[(R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1Hpyrrol-2(5H)-one 
• 1268344-96-2 5-hexyl-1-[(R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1Hpyrrol-2(5H)-one 

Relevant articles and documents

Monoamine oxidase inhibiting activity of a series of (±) 4 methoxy β hydroxyphenethylamines

The synthesis and selected pharmacological testing of (±) 4 methoxy β hydroxyphenethylamine [1 (4 methoxyphenyl) 2 aminoethanol] and its N methylated derivatives are presented. Members of this series were found to exert partial prevention of reserpine induced hypothermia in mice and to inhibit monoamine oxidase in Warburg studies. Activity was essentially dose dependent. The secondary amine was the most active member of the series. The tertiary amine was least active, and the primary amine exhibited intermediate activity.

Bioproduction of Enantiopure (R)- and (S)-2-Phenylglycinols from Styrenes and Renewable Feedstocks

Enantiopure (R)- and (S)-2-phenylglycinols are important chiral building blocks for pharmaceutical manufacturing. Several chemical and enzymatic methods for their synthesis were reported, either involving multi-step synthesis or starting from a relatively complex chemical. Here, we developed one-pot simple syntheses of enantiopure (R)- and (S)-2-phenylglycinols from cheap starting materials and renewable feedstocks. Enzyme cascades consisting of epoxidation-hydrolysis-oxidation-transamination were developed to convert styrene 2 a to (R)- and (S)-2-phenylglycinol 1 a, with butanediol dehydrogenase for alcohol oxidation as well as BmTA and NfTA for (R)- and (S)-enantioselective transamination, respectively. The engineered E. coli strains expressing the cascades produced 1015 mg/L (R)-1 a in >99% ee and 315 mg/L (S)-1 a in 91% ee, respectively, from styrene 2 a. The same cascade also converted substituted styrenes 2 b–k and indene 2 l into substituted (R)-phenylglycinols 1 b–k and (1R, 2R)-1-amino-2-indanol 1 l in 95–>99% ee. To transform bio-based L-phenylalanine 6 to (R)-1 a and (S)-1 a, (R)- and (S)-enantioselective enzyme cascades for deamination-decarboxylation-epoxidation-hydrolysis-oxidation-transamination were developed. The engineered E. coli strains produced (R)-1 a and (S)-1 a in high ee at 576 mg/L and 356 mg/L, respectively, from L-phenylalanine 6, as the first synthesis of these compounds from a bio-based chemical. Finally, L-phenylalanine biosynthesis pathway was combined with (R)- or (S)-enantioselective cascade in one strain or coupled strains, to achieve the first synthesis of (R)-1 a and (S)-1 a from a renewable feedstock. The coupled strain approach enhanced the production, affording 274 and 384 mg/L (R)-1 a and 274 and 301 mg/L (S)-1 a, from glucose and glycerol, respectively. The developed methods could be potentially useful to produce these high-value chemicals from cheap starting materials and renewable feedstocks in a green and sustainable manner. (Figure presented.).

NEGATIVE ALLOSTERIC MODULATION OF GLUN3-CONTAINING N-METHYL-D-ASPARTATE RECEPTORS

Disclosed are negative allosteric modulators of GluN3-containing NMDA receptors. In general, these compounds are highly selective for GluN3 (such as GluN3A and/or GluN3B) over GluN1 and/or GluN2. They can function as non-competitive antagonists with activity that is independent of membrane potential, glycine concentration, and extracellular pH. Also disclosed are pharmaceutical formulations of the negative allosteric modulators. These compounds can be used to enhance synaptic function and/or treating a neurological condition or disorder. Exemplary neurological conditions or disorders include, but are not limited to, major mental disorders, conditions that involve basal ganglia or altered dopamine, substance abuse/addiction or predisposition to substance abuse/addiction, pain disorders, developmental delay or situations with impaired learning, memory, and/or cognition, acute neuronal or glial injuries, and circuit disorders.

Catalytic β C-H amination: Via an imidate radical relay

The first catalytic strategy to harness imidate radicals for C-H functionalization has been developed. This iodine-catalyzed approach enables β C-H amination of alcohols by an imidate-mediated radical relay. In contrast to our first-generation, (super)stoichiometric protocol, this catalytic method enables faster and more efficient reactivity. Furthermore, lower oxidant concentration affords broader functional group tolerance, including alkenes, alkynes, alcohols, carbonyls, and heteroarenes. Mechanistic experiments interrogating the electronic nature of the key 1,5 H-atom transfer event are included, as well as probes for chemo-, regio-, and stereo-selectivity.

Dearomative [2,3] sigmatropic rearrangement of ammonium ylides followed by 1,4-elimination to form α-(ortho-vinylphenyl)amino acid esters

A base-induced dearomative [2,3] sigmatropic rearrangement of amino acid ester-derived ammonium salts followed by 1,4-elimination produced α-(ortho-vinylphenyl)amino acid esters. The reaction of azetidine-2-carboxylic acid-derived ammonium salt, (1S,2S,1′R)-3b, proceeded with a perfect N-to-C chirality transfer to afford α-(ortho-vinylphenyl)azetidine-2-carboxylic acid ester, (R)-5 (99% ee). On the other hand, the reaction of glycine-derived ammonium salt (R)-6a, which involves an efficient chirality transfer from a chiral benzylic carbon to an α-carbon of an ester carbonyl giving the optically active α-(ortho-vinylphenyl)glycine ester, (R)-8a (85% ee), was demonstrated. Although this dearomative [2,3] rearrangement followed by 1,4-elimination has limitations with regard to the structures of the substrates, our method provides unique access to substituted α-arylamino acid derivatives.

Directed β C-H Amination of Alcohols via Radical Relay Chaperones

A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.

Ru-Catalyzed highly diastereoselective hydrogenation of: N-tert -butylsulfinyl ketimines for the synthesis of aryl glycine derivatives

A ruthenium pincer catalyst has been shown to be highly efficient for the hydrogenation of a wide range of α-ketimino esters derived from α-keto esters and chiral 2-methylpropyl-2-sulfinamide, affording chiral aryl glycine derivatives with high yields and diasteroselectivities (20 examples, dr values up to 99:1).

Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water

A practical and convenient method for the efficient and regio- and stereoselective ring-opening of enantiopure monosubstituted epoxides by sodium azide under hydrolytic conditions is reported. The ring-opening of enantiopure styryl and pyridyl (S)-epoxides by N3- in hot water takes place preferentially at the internal position with complete inversion of configuration to produce (R)-2-azido ethanols with up to 99% enantio- and regioselectivity, while the (S)-adamantyl oxirane provides mainly the (S)-1-adamantyl-2-azido ethanol in excellent yield. In general, 1,2-amino ethanols were obtained in high yield and excellent enantiopurity by the reduction of the chiral 1,2-azido ethanols with PPh3 in water/THF, and then converted into the Boc or acetamide derivatives.

Valine amide carbamate derivative containing propargyloxy group and application thereof

The invention relates to a valine amide carbamate derivative containing a propargyloxy group and a pharmaceutically acceptable salt thereof, belonging to the field of botanical bactericides. The valine amide carbamate derivative has a general formula (I) as shown in the specification, and the substituent R in the general formula (I) is as defined in the specification. The invention also relates to a preparation method for the compound as shown in the general formula (I), an intermediate specially prepared for development of the compound and application of the compound to prevention and treatment of plant diseases.

Discovery and optimization of Lu AF58801, a novel, selective and brain penetrant positive allosteric modulator of alpha-7 nicotinic acetylcholine receptors: Attenuation of subchronic phencyclidine (PCP)-induced cognitive deficits in rats following oral administration

In this Letter, we describe a chemical lead optimization campaign starting from a novel, weak α7 nicotinic acetylcholine receptor positive allosteric modulator (PAM) hit from a HTS screen. Exploration of the structure-activity relationships for α7 PAM potency, intrinsic hepatic clearance, the structure-property relationships for lipophilicity, and thermodynamic solubility, led to the identification of Lu AF58801: a potent, orally available, brain penetrant PAM of the α7 nicotinic acetylcholine receptor, showing efficacy in a novel object recognition task in rats treated subchronically with phencyclidine (PCP).