Synthesis Of Β-amino Alcohols Research Articles

Synthesis of β-amino alcohols by ring opening of epoxides with amines catalyzed by sulfated tin oxide under mild and solvent-free conditions

One significant and elegant method for creating β-amino alcohols, which are useful intermediates for the synthesis of many different natural and synthetic pharmaceutical compounds, is to open the rings of epoxides with amines. When sulfated tin oxide catalyst (2 mol%) is present, epoxides can open their rings and react with amines to produce corresponding β-amino alcohols in good to high yields under mild circumstances. Under clean circumstances and in a short amount of time, the reaction demonstrated high regioselectivity and functioned well with both aromatic and aliphatic amines at room temperature.

Negative allosteric modulators of NMDA receptors with GluN2B subunit: synthesis of β-aminoalcohols by epoxide opening and subsequent rearrangement.

In order to obtain novel antagonists of GluN2B subunit containing NMDA receptors, aryloxiranes were opened with benzylpiperidines. Phenyloxiranes 6 and (indazolyl)oxirane 15 were opened regioselectively at the position bearing the aryl moiety. Reaction of the resulting β-aminoalcohols 7 and 16 with carboxylic acids under Mitsunobu conditions (DIAD, PPh3) led to rearrangement and after ester hydrolysis to the regioisomeric β-aminoalcohols 9 and 18. This strategy allows the synthesis of amino-ifenprodil 12 as well using phthalimide in the Mitsunobu reaction. Unexpectedly, the isomeric (indazolyl)oxirane 21 reacted with benzylpiperidines to afford both regioisomeric β-aminoalcohols 22 and 23. In radioligand receptor binding studies, the indazolyl derivative 18a, which can be regarded as indazole bioisostere of ifenprodil, showed high GluN2B affinity (Ki = 31 nM). Replacement of the benzylic OH moiety of ifenprodil by the NH2 moiety in amino-ifenprodil 12 also resulted in low nanomolar GluN2B affinity (Ki = 72 nM). In TEVC experiments, 18a inhibited the ion flux to the same extent as ifenprodil proving that the phenol of ifenprodil can be replaced bioisosterically by an indazole ring maintaining affinity and inhibitory activity. Whereas 10-fold selectivity was found for the ifenprodil binding site over σ1 receptors, only low preference for the GluN2B receptor over σ2 receptors was detected. The log D7.4 value of 18a (log D7.4 = 2.08) indicates promising bioavailability.

Synthesis of β-Amino Alcohols from Value-Added Plant-Polyphenols Using ACC as a Green Reaction Medium and Mechanistic Study from DFT Analysis

A simple, new, and cost-efficient alternative route has been designed for the synthesis of unique β-amino alcohols under metal-free condition from new type of 1,2- disubstituted styrene epoxides obtained from substituted p-hydroxycinnamic acids via greener approach. It was followed by density functional theory (DFT) based computational study to investigate the mechanistic path for generating acetylated amino alcohols i.e. the main key step for the formation of β-amino alcohols.

Synthesis of β-Amino Alcohols by Visible-Light-Assisted Intramolecular Copper-Catalyzed C–H Amination

Synthesis of β-Amino Alcohols by Visible-Light-Assisted Intramolecular Copper-Catalyzed C–H Amination

Active Copper Catalyzed Regioselective Ring Opening of Epoxides by Heterocyclic Amines: An Efficient Protocol for Synthesis of β-Amino Alcohols

The regioselective epoxide ring opening at less substituted carbon atom of epoxide were reported by nucleophiles like heterocyclic amines which gives well known 1,2-difunctionalized amino alcohols. These are present in many synthetic as well as natural products. The ring opening of epoxide is achieved by cleavage with amines in presence of copper(0) as a catalyst. It is observed that the lithium napthalenide reduction of copper(I) produces a highly reactive form of copper(0) that acts as a catalyst for ring opening of epoxides with an amine.

Enantioselective Synthesis of β-Amino Alcohols by Palladium Catalysis

Enantioselective Synthesis of β-Amino Alcohols by Palladium Catalysis

Greener aminolysis of epoxides on BiCl3/SiO2

The remarkable catalytic activity of BiCl 3 /SiO 2 for the ring-opening of epoxides with aromatic and aliphatic amines under microwave and thermal heating was observed. This eco-friendly heterogeneous catalyst displayed high to excellent regioselectivity in the synthesis of β-amino alcohols under solvent-free conditions. High turnover frequency (TOF) values under microwave heating and excellent reusability of the catalyst may significantly contribute to applied chemistry. BiCl 3 /SiO 2 catalyzed regioselective ring-opening of epoxides with aromatic and aliphatic amines.

Enantioselective syntheses of β-amino alcohols catalyzed by recyclable chiral Fe(iii) metal complex

An efficient asymmetric desymmetrization of meso-epoxides with anilines catalyzed by a series of simple and environmentally benign in situ generated Fe(iii) complexes based on chiral tridentate ligands L1–L7 was carried out at rt.

Catalytic metallodendrimers grafted on mesoporous polymethacrylate beads for the regioselective synthesis of β-amino alcohols under solvent-free conditions

Metallodendrimer-grafted mesoporous polymethyacrylate beads for the regioselective, solvent-free, efficient and scalable catalytic synthesis of β-amino alcohols at ambient temperature.

Asymmetric Synthesis of β-Amino Alcohol via Epoxide Ring Opening

Asymmetric Synthesis of β-Amino Alcohol via Epoxide Ring Opening

Synthesis of β-amino alcohols catalyzed by poly(vinyl chloride)-supported Schiff base metal complexes

Eight transition metal complexes of various Schiff bases supported on poly(vinyl chloride) (PVC) were prepared and characterized. These metal complexes were screened as heterogeneous catalysts in the synthesis of β-amino alcohols by ring opening of epoxides with amines. The best catalyst was identified as a Ni(II) complex of PVC-supported 2-[(2-aminoethylimino)methyl]phenol and it was used in the synthesis of a number of different β-amino alcohols. The catalyst was found to be reusable for up to five cycles.

Synthesis of β-Amino Alcohols from Terminal Epoxy Fatty Acid Methyl Ester

Fats and oils are renewable feedstock that can be treated chemically or enzymatically to derive materials that often act as a replacement for petroleum-derived materials. Long-chain fatty epoxides can be transformed to several chemical derivatives. There has been increasing interest in using these substances as intermediates in the production of new biobased industrial materials. In the present work, renewable methyl 10,11-epoxyundecanoate were reacted with various cyclic, aliphatic, and aromatic amines in the presence of zinc(II) perchlorate hexahydrate as a Lewis acid catalyst under solvent-free conditions, to derive several new β-amino alcohols in a regioselective manner.

Mg(ClO4)2, an Efficient Catalyst for Synthesis of β-Amino Alcohols by Ring Opening of Epoxides with Amines under Solvent-Free Conditions

Commercially available magnesium perchlorate is reported as an extremely efficient catalyst for the ring-opening reaction of epoxide with various primary and secondary amines, especially diphenyl amine, under solvent-free conditions at room temperature.

Synthesis of β-amino alcohols by ring opening of epoxides with amines catalyzed by cyanuric chloride under mild and solvent-free conditions

The 2,4,6-trichloro-1,3,5-triazine catalyzed synthesis of β-amino alcohols by aminolysis of epoxide under solvent-free condition is described. Mild reaction conditions, short reaction times, inexpensive and readily available catalysts, and excellent yields of the products with high regioselectivity are attractive features of this methodology.

Synthesis of β-Amino Alcohols from Methyl Epoxy Stearate

Oils and fats are an important source of renewable raw materials, and the availability of functionalized fatty acids such as epoxy ring containing fatty acids gives us a convenient source of starti...

Preparative synthesis of β-amino alcohols from α-amino dicarboxylic acid derivatives

A low-expensive preparative procedure has been developed for the synthesis of protected β-amino alcohols from α-amino dicarboxylic acid derivatives.

Synthesis of β-Amino Alcohols via the Reduction of Lactamides Derived from Ethyl (2S)-Lactate with Borane-Methyl Sulfide

Reactions of ethyl (2S)-lactate with various amines affords lactamides that are reduced with borane-methyl sulfide in the presence of boron trifluoride etherate to generate enantiomerically pure β-amino alcohols in good yield.

B2O3/Al2O3 as an Efficient and Recyclable Catalyst for the Synthesis of β-Amino Alcohols under Solvent-Free Conditions

A convenient and efficient procedure for the solvent-free synthesis of β-amino alcohols has been achieved via B2O3/Al2O3-promoted highly regioselective ring opening of epoxides with aromatic amines in good to excellent yields at room temperature. Additionally, the catalyst can be recycled without affecting the catalytic property.

Synthesis of β-amino alcohols using MgO as a new catalyst under solvent-free conditions

MgO catalyzed efficiently the ring opening of epoxides with a range of aromatic and aliphatic amines to produce β-substituted alcohols in high yields under solvent-free conditions. Exclusive trans stereoselectivity is observed for cyclic epoxide.Key words: MgO, β-amino alcohols, solvent-free, epoxide, amine.

Regio- and stereoselective synthesis of β-amino alcohols over titanosilicate molecular sieves

A novel application of titanosilicate molecular sieves in the synthesis of β-amino alcohols via aminolysis of epoxides, at mild and solvent-free conditions, is reported, for the first time. A range of β-amino alcohols with nearly 100% regio- and stereoselectivity was produced over these reusable solid catalysts in high yields.