cas 124-68-5, 2-Amino-2-methyl-1-propanol | Articles data

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A simple total synthesis of naturally occurring hydroxy-amino acids by enzymatic kinetic resolution
Both optically pure enantiomers of GABOB and isoserine were obtained by enzymatic kinetic resolution of acetylated precursors in three or four steps. The key intermediates were cyanohydrins available from simple aldehydes. This procedure can be applied to other unusual hydroxy amino acids widely distributed in biologically important peptides.
Lu,Miet,Kunesch,Poisson
p. 893 - 902
(1993)
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Cyclization of vinyl ethers derived from amino alcohols
Cyclization of vinyl ethers derived from linear and cyclic α- and β-amino alcohols, catalyzed by mercury(II) acetate gave 2-methyloxazolidines and 2-methylperhydro-1,3-oxazines in 37-94% yield.
Kukharev,Stankevich,Klimenko,Kukhareva
p. 966 - 969
(2007)
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Synthesis and characterization of lanthanide complexes prepared with 2-((E)-(1-hydroxy-2-methylpropan-2-ylimino)methyl)-6-methoxyphenol
Rare-earth complexes of the general formula [Ln(H2L1)2(NO3)3] [Ln?=?Gd (1), Ho (2) or Nd (3)] were prepared from an o-vanillin derived Schiff base ligand, 2-((E)-(1-hydroxy-2-methylpropan-2-ylimino)methyl)-6-methoxyphenol (H2L1). The single-crystal X-ray diffraction studies and SHAPE analyses of the Gd(III) and Ho(III) complexes show that the complexes are ten-coordinate and exhibit distorted tetradecahedron geometries. The phenolate oxygen-bridged dinuclear complex, [Ce2(H2L1)(ovan)3(NO3)3] (4, ovan?=?monodeprotonated o-vanillin), was obtained from the reaction of Ce(NO3)3?6H2O with H2L1. X-ray analysis revealed that hydrolysis of H2L1 occurred to yield o-vanillin, which bridged two cerium atoms with the Ce?Ce distance equal to 3.8232(6) ?. The Ce(III) ions are both ten-coordinate, but have different coordination environments, showing tetradecahedron and staggered dodecahedron geometries, respectively. With proton migration occurring from the phenol group to the imine function, complexation of the lanthanides to the ligand gives the Schiff base a zwitterionic phenoxo-iminium form.
Abrahams, Abubak'r,Madanhire, Tatenda,Hosten, Eric,Betz, Richard
p. 1994 - 2014
(2017)
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Preparation method of 2-amino-2-methyl-1-propanol
The invention discloses a preparation method of 2-amino-2-methyl-1-propanol, which comprises the following preparation steps: adding 2, 2-dimethyl aziridine into a slightly acidic water system, and reacting at the temperature of below 50 DEG C to obtain a reactant; and neutralizing, roughly distilling and rectifying the reactant to obtain the 2-amino -2-methyl-1-propanol. The method has the advantages of mild reaction conditions, simplicity in operation, easiness in mastering, easiness in treatment of the reaction product, high product purity (the purity is 99.0% or above), high yield (the total yield is 90% or above).
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Paragraph 0056-0059

(2021/03/11)

Copper(I) Phosphinooxazoline Complexes: Impact of the Ligand Substitution and Steric Demand on the Electrochemical and Photophysical Properties
A series of seven homoleptic CuI complexes based on hetero-bidentate P^N ligands was synthesized and comprehensively characterized. In order to study structure–property relationships, the type, size, number and configuration of substituents at the phosphinooxazoline (phox) ligands were systematically varied. To this end, a combination of X-ray diffraction, NMR spectroscopy, steady-state absorption and emission spectroscopy, time-resolved emission spectroscopy, quenching experiments and cyclic voltammetry was used to assess the photophysical and electrochemical properties. Furthermore, time-dependent density functional theory calculations were applied to also analyze the excited state structures and characteristics. Surprisingly, a strong dependency on the chirality of the respective P^N ligand was found, whereas the specific kind and size of the different substituents has only a minor impact on the properties in solution. Most importantly, all complexes except C3 are photostable in solution and show fully reversible redox processes. Sacrificial reductants were applied to demonstrate a successful electron transfer upon light irradiation. These properties render this class of photosensitizers as potential candidates for solar energy conversion issues.
Frey, Wolfgang,Giereth, Robin,Karnahl, Michael,Klo?, Marvin,Mengele, Alexander K.,Steffen, Andreas,Tschierlei, Stefanie
p. 2675 - 2684
(2020/03/04)

Palladium-Catalyzed Oxidation of β-C(sp3)-H Bonds of Primary Alkylamines through a Rare Four-Membered Palladacycle Intermediate
Site-selective functionalizations of C-H bonds are often achieved with a directing group that leads to five- or six-membered metallacyclic intermediates. Analogous reactions that occur through four-membered metallacycles are rare. We report a challenging palladium-catalyzed oxidation of primary C-H bonds β to nitrogen in an imine of an aliphatic amine, a process that occurs through a four-membered palladacyclc intermediate. The success of the reaction relies on the identification, by H/D exchange, of a simple directing group (salicylaldehyde) capable of inducing the formation of this small ring. To gain insight into the steps of the catalytic cycle of this unusual oxidation reaction, a series of mechanistic experiments and density functional theory (DFT) calculations were conducted. The experimental studies showed that cleavage of the C-H bond is rate-limiting and formation of the strained four-membered palladacycle is thermodynamically uphill. DFT calculations corroborated these conclusions and suggested that the presence of an intramolecular hydrogen bond between the oxygen of the directing group and hydroxyl group of the ligating acetic acid is crucial for stabilization of the palladacyclic intermediate.
Bunescu, Ala,Ernst, Martin,Hartwig, John F.,Qiu, Yehao,Su, Bo,Zuend, Stephan J.
supporting information
p. 7912 - 7919
(2020/05/22)

PROCESS FOR PRODUCING SUBSTITUTED AMINO ALCOHOLS
The present invention relates to a process for producing a compound of the formula (I) comprising at least the process step: a) reacting a compound of the formula (II) with hydrogen and water in the presence of at least one homogeneous transition metal catalyst TMC 1.
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Page/Page column 33-36

(2020/06/01)

PROCESS FOR PREPARATION OF AMINO ALCOHOLS
A process for the preparation of amino alcohols includes condensing a compound of Formula (II), a stereoisomer, a tautomer, or a salt thereof with a compound of Formula (IlIa) or Formula (Illb), a stereoisomer, a tautomer, or a salt thereof to form a condensation product; hydroxylating or acyloxylating the condensation product in the presence of an oxidant to obtain a hydroxylation or acyloxylation product; and subjecting the hydroxylation or acyloxylation product to one or more subsequent reactions comprising a hydrolysis reaction, alcohol deprotection, an amino lysis reaction, or a combination of two or more thereof to obtain an amino alcohol of Formula (I).
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Paragraph 0050; 0051

(2020/01/31)

Ruthenium-Catalyzed Deaminative Hydrogenation of Amino Nitriles: Direct Access to 1,2-Amino Alcohols
A new approach for the efficient and highly selective synthesis of 1,2-amino alcohols by direct reductive hydrolysis of N-formyl-protected α-amino nitriles is reported. The commercially available RuHCl(CO)(PPh3)3 complex was found to be a suitable catalyst for this operationally simple protocol, in which no stoichiometric amounts of undesired metal waste are generated. The deaminative hydrogenation is performed at 55 bar of H2, using a 6:1 mixture of 1,4-dioxane/water as solvent. In addition, hydroxymethyl alcohols were prepared from cyanoketones under very similar conditions.
Calleja, Pilar,Ernst, Martin,Hashmi, A. Stephen K.,Schaub, Thomas
supporting information
p. 9498 - 9503
(2019/04/30)

Green synthesis method for one-pot process preparation of AMP-95
The invention discloses a green synthesis method for the one-pot process preparation of AMP-95. The method comprises the following steps: S1, preparing 2-nitropropane from acetone, hydrogen peroxide and ammonia in an alcohol solution under the catalysis of a catalyst; S2, directly reacting a reaction solution obtained in step S1 with formaldehyde or paraformaldehyde under an alkaline condition without purifying in order to generate 2-nitro-2-methyl-1-propanol; and S3, directly hydrogenating the reaction product obtained in step S2 without purifying to obtain the product 2-amino-2-methy-1-propanol (AMP-95), and rectifying the product to make the purity reach 99.5% or more. The method has the advantages of cheap and easily available raw materials, simple reaction steps, small pollution to the environment, low cost, high yield, easiness in purification of the product, and suitableness for industrial production.
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Paragraph 0033; 0035; 0037; 0039; 0041; 0043; 0045; 0046

(2018/07/07)

Method for preparing 2-amino-2-methyl-1-propanol
The invention relates to a method for preparing 2-amino-2-methyl-1-propanol. The method comprises the following steps: 1) enabling 2-chloropropane and sodium cyanide to react to generate 2-methyl propionitrile; 2) performing aldol condensation reaction on the 2-methyl propionitrile and formaldehyde so as to generate 2,2-dimethyl-3-hydroxy propionitrile; 3) performing hydrolysis reaction on 2,2-dimethyl-3-hydroxy propionitrile so as to generate 2,2-dimethyl-3-hydroxy propanamide; and 4) performing Hofmann degradation on the 2,2-dimethyl-3-hydroxy propanamide, thereby obtaining 2-amino-2-methyl-1-propanol. The method is cheap and easy in obtaining of raw materials of different steps, simple in reaction process, free of hash reaction condition, remarkable in cost advantage, high in yield, low in pollution and easy in product purification.
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Paragraph 0034; 0038; 0039; 0044; 0045; 0050; 0051

(2017/09/13)

Method for synthesizing 2- amino-2-methyl-1-propanol from isopropylamine
The present invention relates to a method for synthesizing 2-amino-2-methyl-1-propanol from isopropylamine. The isopropylamine reacts with syngas in the presence of a metal catalyst, a ligand and a solvent at the temperature of 100-200 DEG C and at the pressure of 0.8-20 MPa so as to obtain the 2-amino-2-methyl-1-propanol. According to the method, the reactive strategies of metal catalyst in situ preparation, amidogen alpha-position C-H bond activation and hydrogenation one-pot procedure are adopted, the method is wide in raw material resources, simple in steps, mild in condition and easy in separation, and the yield can reach 93%, so that the method is suitable for industrial production.
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Paragraph 0060; 0061; 0062

(2016/10/20)

A Short Access to Symmetrically α,α-Disubstituted α-Amino Acids from Acyl Cyanohydrins
A straightforward synthesis of symmetrically α,α-disubstituted α-amino acids is presented. The key step of this process relies on the efficient double addition of Grignard reagents to acyl cyanohydrins to provide N-acyl amino alcohols selectively in good yields. The chemoselectivity of the reaction was modulated by the nature of the acyl moiety. Eleven amino acids were prepared, including the particularly simple divinylglycine, which is not easily accessible by using conventional methods.
Boukattaya, Fatma,Caillé, Julien,Ammar, Houcine,Rouzier, Florian,Boeda, Fabien,Pearson-Long, Morwenna S. M.,Bertus, Philippe
p. 906 - 916
(2016/03/12)

Process and Apparatus For Production And Filtration Of Aminoalcohols Using A Continuous Stirred Tank Slurry Reactor
Disclosed are processes and apparatuses for producing a reaction product and enabling the reaction product to be removed from a reactor operating at an elevated pressure, while simultaneously maintaining the gas pressure and retaining the catalyst inside the apparatus.
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Paragraph 0024

(2014/05/08)

Carbon dioxide capture and use: Organic synthesis using carbon dioxide from exhaust gas
A carbon capture and use (CCU) strategy was applied to organic synthesis. Carbon dioxide (CO2) captured directly from exhaust gas was used for organic transformations as efficiently as hyper-pure CO2 gas from a commercial source, even for highly air- and moisture-sensitive reactions. The CO2 capturing aqueous ethanolamine solution could be recycled continuously without any diminished reaction efficiency. Exhaust gas is good enough! Carbon dioxide captured directly from exhaust gas was used for organic syntheses (see picture) as efficiently as hyper-pure CO2 gas from a commercial source, even for highly air- and moisture-sensitive reactions. The CO2 capturing aqueous ethanolamine solution could be recycled continuously without any diminished reaction efficiency. Copyright
Kim, Seung Hyo,Kim, Kwang Hee,Hong, Soon Hyeok
supporting information
p. 771 - 774
(2014/01/23)

PROCESS FOR MAKING AMINOALCOHOL COMPOUNDS
Provided is a process for making an aminoalcohol compound. The process comprises using an excess amount of aliphatic aldehyde in a condensation step between the aldehyde and a nitroalkane, and using an aldehyde scavenger in a reductive hydrogenation step. The process yields aminoalcohol compounds exhibiting reduced color and odor.
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Page/Page column 5-6

(2011/10/04)

Versatile synthesis of free and N-benzyloxycarbonyl-protected 2,2-disubstituted taurines
An effective and versatile method was developed to synthesize N-benzyloxycarbonyl-protected and free 2,2-disubstituted taurines. Several novel 2,2-disubstituted taurines, including aliphatic/aromatic and cyclic/acyclic derivatives, were obtained, which demonstrates the generality of this method. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Wang, Boyuan,Zhang, Wei,Zhang, Leilei,Du, Da-Ming,Liu, Gang,Xu, Jiaxi
p. 350 - 355
(2008/09/18)

A catalyst-free, convenient construction of eight-membered [1,4]oxazocane-5,8-dione heterocycles from aminoethanols with divinyl succinate
A convenient protocol for the synthesis of [1,4]oxazocane-5,8-dione heterocycles by direct cyclization using 2-substituted aminoethanols and divinyl succinate without any catalysts and additives was established. This strategy is quite simple and effective to obtain eight-membered rings incorporating lactone and lactam functional groups. Georg Thieme Verlag Stuttgart.
Chen, Wan-Qin,Zhang, Qing-Yi,Liu, Bo-Kai,Wu, Qi,Lin, Xian-Fu
scheme or table
p. 1829 - 1832
(2009/04/07)

Nanomolar β-lactamase inhibitors
New carboxyphenyl-glycylboronic acid transition-state analog inhibitors, representative of a class of compounds effective against class C β-lactamase AmpC. The new compounds improve inhibition by over two-orders of magnitude compared to analogous glycylboronic acids, with Ki values as low as 1 nM.
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Page/Page column 33

(2010/11/28)

NOVEL LYSOPHOSPHATIDIC ACID RECEPTOR SELECTIVE ANTAGONISTS
The present invention is directed to compositions comprising lysophosphatidic acid analogs and methods of using such analogs as agonist or antagonists of LPA receptor activity. In addition the invention is directed to LPA receptor agonists that vary in the degree of selectivity at individual LPA receptors (i.e. LPA1, LPA2 and LPA3). More particularly the present invention is directed to LPA analogs wherein the glycerol is replaced with ethanolamine and a variety of substitutions have been linked at the second carbon atom.
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Page/Page column 76

(2008/06/13)

Hair growth stimulant
The present invention provides a hair growth agent and a hair fostering shampoo that have N-methyltaurine as an essential ingredient, and have hair growth period extending effects, and moreover are capable of giving hair fitness and body and giving hair a feeling of volume. Moreover, the present invention also provides a cell activating agent and a hair fitness/body improving agent that are blended into hair cosmetics.
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(2008/06/13)

SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS
The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed
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(2008/06/13)

Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents
This invention relates to 2-arylimino heterocycles, including 2-arylimino-1,3-thiazolidines, 2-arylimino-2,3,4,5-tetrahydro-1,3-thiazines, 2-arylimino-1,3-thiazolidin-4-ones, 2-arylimino-1,3-thiazolidin-5-ones, and 2-arylimino-1,3-oxazolidines, and their use in modulating progesterone receptor mediated processes, and pharmaceutical compositions for use in such therapies.
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Page column 138

(2010/02/05)

2,3-oxidosqualene-lanosterol cyclase inhibitors
The present invention relates to aminocyclohexanol derivatives useful for the treatment and/or prophylaxis of diseases which are associated with 2,3-oxidosqualene-lanosterol cyclase such as hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, gallstones, tumors and/or hyperproliferative disorders, and treatment and/or prophylaxis of impaired glucose tolerance and diabetes.
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(2008/06/13)

Catalytic Hydrogenation of Chiral α-Amino and α-Hydroxy Esters at Room Temperature with Nishimura Catalyst without Racemization
The hydrogenation of carboxylic acid derivatives at room temperature was investigated. With a mixed Rh/Pt oxide (Nishimura catalyst), low to medium activity was observed for various α-amino and α-hydroxy esters. At 100 bar hydrogen pressure and 10% catalysts loading, high yields of the desired amino alcohols and diols were obtained without racemization. The most suitable α-substituents were NH2, NHR, and OH, whereas β-NH2 were less effective. Usually, aromatic rings were also hydrogenated, but with the free bases of amino acids as substrates, some selectivity was observed. No reaction was found for α-NR2, α-OR, and unfunctionalized esters; acids and amides were also not reduced under these conditions. A working hypothesis for the mode of action of the catalyst is presented.
Studer, Martin,Burkhardt, Stefan,Blaser, Hans-Ulrich
p. 802 - 808
(2007/10/03)

2-benzyl-polycyclic guanine derivatives and process for preparing them
Antihypertensive and bronchodilating compounds of the formula or a pharmaceutically acceptable salt thereof, and a process for preparing them are disclosed, wherein: R1, R2, R3, Ra, Rb and Rc as defined in the disclosure; pharmaceutical compositions containing said compounds; methods of treatment using said compounds; and a process for preparing polycyclic guanines comprising a) reducing a nitrosopyrimidine, and treating the reduced nitrosopyrimidine with an acylating reagent to give the amidopyrimidine; b) reacting the amidopyrimidine with a halogenating/cyclizing reagent to give a halopurine; c) reacting, in the presence of a base, the halopurine with an amine to give the substituted aminopurine; and d) closing the ring of the substituted aminopurine with a suitable dehydrating agent.
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(2008/06/13)

Dicationic and polycationic monoprimary alcohols and derivatives thereof
This invention relates to novel dicationic and polycationic monoprimary alcohol compounds and their derivatives, represented by the formula STR1 wherein each alk is independently alkyl of 1-8 carbon atoms; each ALK is independently alkyl of 1-8 carbon atoms; each R1, R2, R3, R4 or R5 is independently H or alkyl of 1-8 carbon atoms; n is 2-5; G is H, CR1 R2 CR3 OHCR4 R5 X or STR2 X is Cl, Br or I; An- is an anion and p is 1-10; provided that the compound is soluble in water.
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(2008/06/13)

Attempted synthesis of substituted 8-oxo-4-oxa-1-azabicyclooctane through intramolecular reductive cyclisation
Reductive intramolecular cyclisation of 2-(N-succinimido)-1-ethanol gives 8-oxo-4-oxa-1-azabicyclooctane in a good yield.On introduction of further substitution of C-1 and C-2 no cyclisation is observed.A mechanistic rational is presented.
Mishra, Shri Krishna,Vani, T R,Rao, R Balaji
p. 641 - 644
(2007/10/02)

INFLUENCE OF SUBSTITUENTS ON THE RATE OF FORMATION OF DICHLORAMINES
The kinetics of the disproportionation reactions of chloramines in water have been studied at acidic pH.Disproportionation and protonation constants and the coefficients of absorption of dichloramines were calculated.The mechanism of disproportionation is discused.
Antelo, Juan Manuel,Arce, Florencio,Parajo, Mercedes,Barro, Pilar Rodriguez
p. 549 - 552
(2007/10/02)

A systematic entropy relationship for the general-base catalysis of the deprotonation of a carbon acid. A quantitative probe of transition-state solvation
The general-base-catalyzed deprotonation of a carbon acid, the l-methyl-4-(phenylacetyl)pyridinium cation (pKa = 9.02 at 25 °C), has been investigated for 32 general-base catalysts (25 amines and seven phenoxide ions) in aqueous solution. Amines give a generally scattered Bronsted plot; ring-substituted benzylamines have ?= 0.52, and ring-substituted phenoxides have ?= 0.60, with the phenoxides being more reactive than amines of similar basicity. The temperature dependences of the general-base-catalyzed deprotonation of this carbon acid have been measured over the range 15-45 °C for 12 base catalysts (eight primary, secondary, and tertiary amines; 4-(dimethylamino)pyridine; two phenoxide ions; hydroxide ion). The entropies of activation for these deprotonations show a clean curvilinear dependence upon the entropies of protonation of these base species, with the hydroxide ion being the only significant deviant from this relationship. This observation quantitatively establishes the importance of solvation effects as the major source of deviations that are commonly observed in Bronsted relationships for general-base-catalyzed processes.
Bunting, John W.,Stefanidis, Dimitrios
p. 779 - 786
(2007/10/02)

Electrochemical Reduction of Tertiary Nitroalkanes to Amines
Electrochemical reduction of tertiary nitroalkanes, 2-substituted-1,1-dimethyl-1-nitroethanes (1), was investigated in aqueous buffer solutions.In polarography, 1 with a phenyl group and/or a hydroxyl group at the 2-position showed an ill-defined wave in the weakly acidic and neutral pH region at relatively high negative potentials, in addition to a well-defined wave arising from the reduction of 1 to the corresponding hydroxylamine (2).Controlled potential electrolysis of 1 at the potential of the former wave gave the 1,1-dimethylethylamines (3) as well as the hydroxylamines 2.The amines 3 are formed exclusively from 2, probably via the O-protonated form.It is suggested that a phenyl group at the 2-position facilitates the reduction of 2 to 3 by enhancing the adsorption of 2 at the mercury cathode and that a hydroxyl group, while it interferes with the adsorption, assists the reduction by intramolecular hydrogen-bonding to stabilize the O-protonated form of 2.Keywords - tertiary nitroalkane; alkylhydroxylamine; electrochemical reduction; polarography; controlled potential electrolysis.
Ohmori, Hidenobu,Furusako, Shoji,Kashu, Mieko,Ueda, Chihiro,Masui, Masaichiro
p. 3345 - 3353
(2007/10/02)

Anodic Oxidation of Amines. VII. Oxidation of β-Alkanolamines in Aqueous Buffer of pH 10
The anodic oxidation of several different types of β-alkanolamines, R1R2C(OH)CR3R4NR5R6, was studied by cyclic voltammetry and controlled potential electrolysis in an aqueous carbonat buffer of pH 10 at a glassy carbon electrode.Upon oxidation, both the (α)C-(β)C and the C-N bonds are cleaved.Substituents R1-R4 affect the first oxidation potential and product distribution.The relative rates of the bond cleavages were estimated from the oxidation products.It was found that most of the amine cleaves through the (α)C-(β)C bond when at least one of the R groups is phenyl, nearly half cleaves through this bond when R is alkyl, and only about a tenth does so when R1-R4 are all hydrogen.The stability of the transient intermediates at the e-c step of the e-c-e process seems to affect the oxidation potentials and to govern the relative rates of the (α)C-(β)C bond cleavage.A scheme for the reaction processes is proposed.Keywords---β-alkanolamines; anodic oxidation; (α)C-(βC) bond fission; C-N bond fission; carbonate buffer; aldehyde; acetone; glycolaldehyde
Masui, Masaichiro,Kamada, Yoshiyuki,Sasaki, Etuko,Ozaki, Shigeko
p. 1234 - 1243
(2007/10/02)

Substituted pyridines
This invention relates to substituted pyridines prepared by reacting aldehydes, amines, lower carboxylic acids such as acetic acid in the presence of oxygen. The N-substituted pyridinium salts formed can be converted to pyridines by thermal dealkylation. The reactions can be summarized by the following equations: STR1
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(2008/06/13)

Process for converting esters to amine salts
A new method for converting certain diesters to physiologically acceptable amines which comprises reacting the diester with the desired amine in a solvent consisting essentially of water.
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(2008/06/13)