27720-05-4

Upstream product

• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 17469-89-5 (2S)-2-(dimethylamino)-3-phenylpropanoic acid 

Downstream Products

• 1350524-92-3 2-(2-(dimethylamino)-3-phenylpropanoyl)-N-phenylhydrazinecarbothioamide 
• 97800-69-6 2-(dimethylamino)-3-phenylpropanehydrazide 
• 19881-91-5 (1-benzyl-2-hydroxy-ethyl)-trimethyl-ammonium; iodide 
• 56755-22-7 L-N,N,N-trimethylphenylalanine 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 27720-03-2 S-2-(Dimethylamino)-3-phenyl-1-propanol 

Relevant academic research and scientific papers

Expedient Synthesis of N-Methyl- and N-Alkylamines by Reductive Amination using Reusable Cobalt Oxide Nanoparticles

N-Methyl- and N-alkylamines represent important fine and bulk chemicals that are extensively used in both academic research and industrial production. Notably, these structural motifs are found in a large number of life-science molecules and play vital roles in regulating their activities. Therefore, the development of convenient and cost-effective methods for the synthesis and functionalization of amines by using earth-abundant metal-based catalysts is of scientific interest. In this regard, herein we report an expedient reductive amination process for the selective synthesis of N-methylated and N-alkylated amines by using nitrogen-doped, graphene-activated nanoscale Co3O4-based catalysts. Starting from inexpensive and easily accessible nitroarenes or amines and aqueous formaldehyde or aldehydes in the presence of formic acid, this cost-efficient reductive amination protocol allows the synthesis of various N-methyl- and N-alkylamines, amino acid derivatives, and existing drug molecules.

Reductive N-methylation of amines with calcium hydride and Pd/C catalyst

The methylation of amines by paraformaldehyde in the presence of calcium hydride as a source of hydrogen and palladium on charcoal as catalyst was studied. Depending on the quantity of paraformaldehyde, monomethylated and dimethylated amines were selectively and efficiently prepared in one pot with good yields.

METHOD OF PRODUCING TERTIARY AMINE OR TERTIARY AMINE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a method of producing tertiary amine or tertiary amine derivative with high selectivity. SOLUTION: In the method of producing tertiary amine or tertiary amine derivative, a reaction system including: an organic chemical raw material containing at least one kind of group selected from -NH2, -NH2 HCl, >NH and >NH HCl, a nitrogen atom contained in the group bounding to a carbon atom; aliphatic alcohol having 1 to 20 carbon atoms; and a catalyst where a carrier containing titanium oxide carries a silver component (metal silver or silver compound), is irradiated with light, and the group in the organic compound raw material is converted to -NR02 or >NR0, ( R0 is an aliphatic hydrocarbon group having 1 to 20 carbon atoms derived from the aliphatic alcohol). The percentage content of the silver in the catalyst is 0.5 to 10 mass% with respect to the titanium oxide. COPYRIGHT: (C)2015,JPOandINPIT

Efficient ruthenium-catalyzed N-methylation of amines using methanol

An in situ-generated complex from [RuCpCl2]2 and dpePhos ligand is reported as an efficient catalyst in the presence of 5 mol % of LiOtBu for the N-methylation of amines using methanol as the methylating agent at moderate conditions, following hydrogen borrowing strategy. This simple catalyst system provides selective N-monomethylation of substituted primary anilines and sulfonamides as well as N,N dimethylation of primary aliphatic amines in excellent yields at 40-100 °C with good tolerance to reducible functional groups. The catalytic intermediate CpRu(dpePhos)H was isolated and was shown to be active for methylation in the absence of base.

Amino acid based chiral N-amidothioureas. Acetate anion binding induced chirality transfer

N-Amidothioureas generated from amine-dimethylated natural l-phenylalanine and its d-enantiomer bearing a chiral carbon that is by 2 atoms or 3 chemical bonds away from the anion binding site establish chiral communication upon acetate anion binding to the thiourea moiety.

Establishment of the absolute configuration of the bioactive marine alkaloid eudistomin X by stereospecific synthesis

The marine β-carboline alkaloid eudistomin X has been synthesised stereospecifically, using d-phenylalanine as the chiral pool starting material, establishing the absolute configuration of the natural product as (10R). A stereospecific synthesis of both e

LiOH-mediated N-monoalkylation of α-amino acid esters and a dipeptide ester using activated alkyl bromides

Selective N-monoalkylation of α-amino esters with activated alkyl bromides was studied using various alkali or alkali earth metal bases. In the production of N-monoalkylated amino ester derivatives and suppression of N,N-dialkylation, lithium hydroxide wa

Diastereoselection during 1,2-Addition of the Allylindium Reagent to α-Thia and α-Amino Aldehydes in Aqueous and Organic Solvents

The stereochemistry of the indium-promoted reaction of allyl bromide with α-thia (PhS and MeS), disubstituted α-amino (Bn2N, Me2N, isoindolyl), and protected α-amino aldehydes (Ac and Boc) in water has been evaluated. The reactions involving the sulfur derivatives are minimally diastereoselective, indicating that the allylindium reagent is not thiophilic. Chelation is not observed and π-facial discrimination is achieved via Felkin - Ahn transition states under the steric control of the substituents. The Garner aldehyde is also anti-diastereoselective. Interestingly, N-acetylmannosamine is appreciably responsive to chelation control and is capable of generating 90% of the syn β-amino alcohol when reacted in a 0.5 M NH4Cl solution. While the α-dibenzylamino substituent is too bulky to enter into complexation, the α-dimethylamino group is not and can lead to high levels (99%) of syn diastereomer. The size of other neighboring substituents does have an impact on π-facial discrimination in these systems and can erode the stereoselectivity accordingly.