Synthesis of 1,2-amino alcohols via catalytic C–H amidation of sp3 methyl C–H bonds

2014 ◽  
Vol 50 (81) ◽  
pp. 12073-12075 ◽  
Author(s):  
Taek Kang ◽  
Heejeong Kim ◽  
Jeung Gon Kim ◽  
Sukbok Chang
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols ◽  
Chelating Groups

A new route to 1,2-amino alcohols is presented by C–H amidation of sp3 methyl C–H bonds as a key step. Various alcohols were employed after converting them to removable ketoxime chelating groups. Iridium-catalyzed C–H amidation and following LAH reduction furnished β-amino alcohol products.

ChemInform Abstract: Synthesis of 1,2- and 1,4-Amino Alcohols from 1,3-Dienes via Oxazines. Rearrangements of 1,4-Amino Alcohol Derivatives to Oxazolines.

ChemInform ◽  
2010 ◽  
Vol 41 (37) ◽  
pp. no-no
Author(s):  
Lukas Werner ◽  
Jason Reed Hudlicky ◽  
Martina Wernerova ◽  
Tomas Hudlicky
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols

Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: 8-Substituted 6-(4-piperidyl)-6H-dibenz[b,e]-1,4-oxathiepins

1982 ◽  
Vol 47 (11) ◽  
pp. 3077-3093 ◽  
Author(s):  
Karel Šindelář ◽  
Jiřina Metyšová ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jiří Protiva ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Amino Alcohol ◽  
Sodium Hydride ◽  
Amino Alcohols ◽  
Central Ring ◽  
Psychotropic Agents ◽  
High Degree ◽  
By Products ◽  
Antiapomorphine Effect ◽  
Central Depressant

2-(2-Fluorophenylthio)benzaldehydes IXa-c and 5-chloro-2-(2-fluorophenylthio)acetophenone were treated with 1-methyl-4-piperidylmagnesium chloride and 3-dimethylaminopropylmagnesium chloride, respectively, and the resulting amino alcohols VIa-c, XVII and XVIII were cyclized with sodium hydride in dimethylformamide. In addition to the title compounds Ia-c, XIX and XX, several types of by-products were obtained. Demethylation of compound Ib by the chloroformate method afforded the secondary amine IIb which was transformed to the amino alcohols IIIb and Vb. Compounds Ia-c are very potent neuroleptics with a high degree of central depressant and cataleptic activity. The amino alcohol Vb exhibits a very strong antiapomorphine effect in rats.

scholarly journals Continuous and convergent access to vicinyl amino alcohols

2015 ◽  
Vol 51 (82) ◽  
pp. 15133-15136 ◽  
Author(s):  
Tomoya Nobuta ◽  
Guozhi Xiao ◽  
Diego Ghislieri ◽  
Kerry Gilmore ◽  
Peter H. Seeberger
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols ◽  
Assembly System

A four module convergent chemical assembly system delivers two classes of vicinyl amino alcohol and five APIs.

Photoredox catalysed synthesis of amino alcohol

2018 ◽  
Vol 42 (1) ◽  
pp. 688-691 ◽  
Author(s):  
Vishal Srivastava ◽  
Pravin K. Singh ◽  
Sudhanshu Kanaujia ◽  
Praveen P. Singh
Keyword(s):  
Visible Light ◽  
Amino Alcohol ◽  
Amino Alcohols ◽  
One Pot

A mild and efficient one-pot visible light-induced method has been developed for the synthesis of amino alcohols.

scholarly journals The Heterogeneous Aminohydroxylation Reaction Using Hydrotalcite-Like Catalysts Containing Osmium

Catalysts ◽  
2018 ◽  
Vol 8 (11) ◽  
pp. 547
Author(s):  
Mohamed Fadlalla ◽  
Glenn Maguire ◽  
Holger Friedrich
Keyword(s):  
Reaction Time ◽  
Amino Alcohol ◽  
Amino Alcohols ◽  
Solvent System ◽  
Precipitation Method ◽  
Reaction Solution ◽  
Heat Treated ◽  
Transformation Reaction ◽  
Significant Difference ◽  
Co Precipitation

The aminohydroxylation reaction of olefins is a key organic transformation reaction, typically carried out homogeneously with toxic and expensive osmium (Os) catalysts. Therefore, heterogenisation of this reaction can unlock its industrial potential by allowing reusability of the catalyst. Os–Zn–Al hydrotalcite-like compounds (HTlcs), as potential heterogeneous aminohydroxylation catalysts, were synthesised by the co-precipitation method and characterised by several techniques. Reaction parameters (i.e., solvent system, reaction temperature, and catalyst structure) were optimized with cyclohexene, styrene, and hexene as substrates. The different classes of olefins (aliphatic, aromatic, and functionalised) that were tested gave >99% conversion and high selectivity (>97%) to the corresponding β-amino alcohol. The catalyst HTlc structure had a significant effect on the reaction time and yield of the β-amino alcohols. Under the same testing conditions, a heat treated catalyst (non-HTlc) showed a shorter reaction time, but drop in the yield of β-amino alcohols and rise in diol formation was observed. Leaching tests showed that 2.9% and 3.4% of Os (inactive) leached from the catalyst to the reaction solution when MeCN/water (1:1 v/v) and t-BuOH/water (1:1 v/v), respectively, were used as the solvent system. Recycling studies showed that the catalyst can be reused at least thrice, with no significant difference in the yield of the β-amino-alcohol.

scholarly journals Microbial metabolism of amino alcohols. Metabolism of ethanolamine and 1-aminopropan-2-ol in species of Erwinia and the roles of amino alcohol kinase and amino alcohol O-phosphate phospho-lyase in aldehyde formation

1973 ◽  
Vol 134 (4) ◽  
pp. 959-968 ◽  
Author(s):  
Alan Jones ◽  
Anne Faulkner ◽  
John M. Turner
Keyword(s):  
Aldehyde Dehydrogenase ◽  
Amino Alcohol ◽  
Erwinia Carotovora ◽  
Microbial Metabolism ◽  
Amino Alcohols ◽  
Growth Media ◽  
N Sources ◽  
N Source ◽  
Erwinia Ananas

1. Growth of Erwinia carotovora N.C.P.P.B. 1280 on media containing 1-aminopropan-2-ol compounds or ethanolamine as the sole N source resulted in the excretion of propionaldehyde or acetaldehyde respectively. The inclusion of (NH4)2SO4 in media prevented aldehyde formation. 2. Growth, microrespirometric and enzymic evidence implicated amino alcohol O-phosphates as aldehyde precursors. An inducibly formed ATP–amino alcohol phosphotransferase was partially purified and found to be markedly stimulated by ADP, unaffected by NH4+ ions and more active with ethanolamine than with 1-aminopropan-2-ol compounds. Amino alcohol O-phosphates were deaminated by an inducible phospho-lyase to give the corresponding aldehydes. This enzyme, separated from the kinase during purification, was more active with ethanolamine O-phosphate than with 1-aminopropan-2-ol O-phosphates. Activity of the phospho-lyase was unaffected by a number of possible effectors, including NH4+ ions, but its formation was repressed by the addition of (NH4)2SO4 to growth media. 3. E. carotovora was unable to grow with ethanolamine or 1-aminopropan-2-ol compounds as sources of C, the production of aldehydes during utilization as N sources being attributable to the inability of the microbe to synthesize aldehyde dehydrogenase. 4. Of seven additional strains of Erwinia examined similar results were obtained only with Erwinia ananas (N.C.P.P.B. 441) and Erwinia milletiae (N.C.P.P.B. 955).

Pd-catalyzed Arylation of 1,2-Amino Alcohol Derivatives via beta-Carbon Elimination

Synlett ◽  
2021 ◽  
Author(s):  
Ruben Martin ◽  
Miguel Pericàs ◽  
Miriam Sau
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols ◽  
Aryl Halides ◽  
Entry Point ◽  
New Entry

Herein, we describe a Pd-catalyzed arylation of 1,2-amino alcohols with aryl halides enabled by a retroallylation manifold. This protocol constitutes a new entry point to beta-arylated aldehydes via the intermediacy of in situ generated enamine intermediates. The protocol is characterized by its exquisite regioselectivity profile and broad substrate scope – including challenging substrate combinations –, even in an enantioselective manner

Oxidation von Methylpiperidin-Derivaten unter Berücksichtigung der Chiralität / Oxidation of Methylpiperidine Derivatives with Regard to Chirality

2007 ◽  
Vol 62 (12) ◽  
pp. 1514-1524 ◽  
Author(s):  
Hans Möhrle ◽  
Thomas Berkenkemper
Keyword(s):  
Nmr Spectroscopy ◽  
Carbon Atom ◽  
Amino Alcohol ◽  
Amino Alcohols ◽  
Pure Form ◽  
Piperidine Ring ◽  
Methyl Groups ◽  
Enantiomerically Pure ◽  
Iminium Salts

When 2-(2-methyl-1-piperidinyl)ethanol derivatives 3a and 3b were dehydrogenated with Hg(II)- EDTA, an iminium function involving the tertiary α-carbon atom of the piperidine ring is formed regioselectively. Cyclization of these intermediates yielded diastereomeric mixtures of oxazolidines 7a and 7b, in solutions of which hydroxy-enamine species 8a/9a and 8b/9b, respectively, could be detected by NMR spectroscopy. A hydroxy-enamine derived from 7a could be trapped by cycloaddition to tetrazine 10. Protonation of the oxazolidines generated the iminium salts 6a/6b・X with loss of a chirality center. For prevention of different directions of ring dehydrogenation in the 2-(3-methyl- 1-piperidinyl)ethanol compounds, the 6-position was blocked with two methyl groups. With amino alcohol 17, the isolation of one of the racemates in pure form was achieved, which by dehydrogenation produced a diastereoisomeric lactam mixture 18, as shown by NMR spectroscopy. Reaction of 2-(4-methyl-1-piperidinyl)ethanol 19 with Hg(II)-EDTA gave rise to a diastereomeric lactam mixture 21 in the ratio 60 : 40. From enantiomerically pure phenyloxiranes, the amino alcohols R(-)-19 and S(+)-19 became available. Their dehydrogenation under standardized conditions always showed a spreading range of isomeric lactams, which could not be separated.

Potential antidepressants: 3-Methyl-6-dimethylamino-1,2-diphenylhexan-3-ol and related compounds

1987 ◽  
Vol 52 (10) ◽  
pp. 2564-2571
Author(s):  
Irena Červená ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Martin Valchář ◽  
Miroslav Protiva
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols ◽  
Related Compounds

3,4-Diphenylbutan-2-one (III) and 3-methyl-3-phenylbutan-2-one were transformed by treatment with 3-dimethylaminopropylmagnesium chloride and 1-methyl-4-piperidylmagnesium chloride to the amino alcohols VI, VII, and X. Compound VI was dehydrated to the olefinic amine VIII, and reduced to the saturated amine IX. 2-(3-Fluoro-4-hydroxyphenyl)ethylamine (XI) was prepared by a modified route via the methoxy precursor XV. Only the amino alcohol VI showed antireserpine activity in one test. The fluoro analogue of dopamine XI did show neither the dopaminomimetic nor the antidopaminergic character.

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