40871-00-9

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 3-(benzylamino)butanoate is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows for the creation of a wide range of molecules with potential therapeutic applications.
Used in Chemical Synthesis:
Methyl 3-(benzylamino)butanoate is used as a key component in the synthesis process for piperidines through iridium-catalyzed cyclocondensation. This method is valuable for the production of complex organic molecules, which can be further utilized in various chemical and pharmaceutical applications.

Upstream product

• 623-43-8 crotonic acid methyl ester 
• 14856-79-2 N-benzyl(trimethylsilyl)amine 
• 96201-10-4 benzyl(tert-butyldimethylsilyl)amine 
• 119645-08-8 N-(diphenylmethylsilyl)benzylamine 
• 113709-50-5 Lithium N-benzyl-N-(trimethylsilyl)amide 
• 100-46-9 benzylamine 
• 113034-33-6 (R)-N-benzyl-β³-homoalanine 
• 623-43-8 methyl crotonate 
• 72002-24-5 3-benzylaminobut-2-enoic acid methyl ester 
• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 5303-65-1 (S)-ethyl 3-aminobutyrate 
• 507444-65-7 methyl 3-(benzylamino)butanoate 
• 109299-92-5 3-((E)-but-2-enoyl)oxazolidin-2-one 

Downstream Products

• 119645-17-9 Benzyl-((E)-3-methoxy-1-methyl-3-trimethylsilanyloxy-allyl)-trimethylsilanyl-amine 
• 98014-60-9 tert-butyl N-benzyl-N-(1-methyl-3-oxopropyl)carbamate 
• 113709-39-0 methyl 3-(benzylamino)-2-methylbutanoate 

Relevant academic research and scientific papers

Solvent engineering: an effective tool to direct chemoselectivity in a lipase-catalyzed Michael addition

A solvent engineering strategy was implemented in order to control the chemoselectivity in a lipase-catalyzed Michael addition reaction. This strategy was revealed as a high-effective tool for the selective synthesis of Michael adduct 3 or aminolysis product 4 from benzylamine 1 and methyl crotonate 2. Chemoselectivity of the enzymatic process was elucidated in terms of polarity of the medium, hence, adduct 3 was preferentially accumulated in hydrophobic medium, whereas in polar solvents the amide 4 was preferentially formed.

ERBB RECEPTOR INHIBITORS

Disclosed are compounds inhibiting ErbBs (e. g. HER2), pharmaceutically acceptable salts, hydrates, solvates or stereoisomers thereof and pharmaceutical compositions comprising the compounds. The compound and the pharmaceutical composition can effectively treat diseases associated ErbBs (especially HER2), including cancer.

TETRAHYDROPYRIDO[4,3-D]PYRIMIDINE INHIBITORS OF ATR KINASE

The present invention relates to tetrahydropyrido[4,3-d]pyrimidine based compounds and methods which may be useful as inhibitors of ATR kinase for the treatment or prevention of cancer.

Mechanochemical enzymatic resolution of N-benzylated-β3-amino esters

The use of mechanochemistry to carry out enantioselective reactions has been explored in the last ten years with excellent results. Several chiral organocatalysts and even enzymes have proved to be resistant to milling conditions, which allows for rather efficient enantioselective transformations under ball-milling conditions. The present article reports the first example of a liquid-assisted grinding (LAG) mechanochemical enzymatic resolution of racemic β3-amino esters employing Candida antarctica lipase B (CALB) to afford highly valuable enantioenriched N-benzylated-β3-amino acids in good yields. Furthermore the present protocol is readily scalable.

One-pot lipase-catalyzed enantioselective synthesis of (r)-(?)-n-benzyl-3-(benzylamino)butanamide: The effect of solvent polarity on enantioselectivity

The use of the solvent engineering has been applied for controlling the resolution of lipase-catalyzed synthesis of β-aminoacids via Michael addition reactions. The strategy consisted of the thermodynamic control of products at equilibrium using the lipase CalB as a catalyst. The enzymatic chemo- and enantioselective synthesis of (R)-(?)-N-benzyl-3-(benzylamino)butanamide is reported, showing the influence of the solvent on the chemoselectivity of the aza-Michael addition and the subsequent kinetic resolution of the Michael adduct; both processes are catalyzed by CalB and both are influenced by the nature of the solvent medium. This approach allowed us to propose a novel one-pot strategy for the enzymatic synthesis of enantiomerically enriched β-aminoesters and β-aminoacids.

METHYL DIAZEPANE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to methyl diazepane compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.

Thermodynamically controlled chemoselectivity in lipase-catalyzed aza-Michael additions

Chemoselective synthesis of N-protected β-amino esters involving lipase-catalyzed aza-Michael additions and α,β-unsaturated precursors is mainly hampered by the two electrophilic sites present on these compounds. In order to control the chemoselectivity a solvent engineering strategy based on the thermodynamic behaviour of products in media of different polarity was designed. This strategy allowed to obtain aza-Michael adducts from benzylamine and different acrylates with high selectivity. In almost all reactions carried out in n-hexane, a non-polar solvent, aminolysis was avoided while the corresponding Michael adducts were exclusively synthesized in 53-78% yields. On the contrary, in reactions carried out in a polar solvent such as 2-methyl-2-butanol the aminolysis products were favoured. Thermodynamic analyses of these processes using the COSMO-RS method helped to understand some of the key factors affecting chemoselectivity and confirmed that a reliable estimation of the thermodynamic interactions of solutes and solvents allows an adequate selection of a reaction media that may lead to chemoselectivity.

Lipase-catalyzed aza-michael reaction on acrylate derivatives

A methodology has been developed for an efficient and selective lipase-catalyzed aza-Michael reaction of various amines (primary and secondary) with a series of acrylates and alkylacrylates. Reaction parameters were tuned, and under the optimal conditions it was found that Pseudomonas stutzeri lipase and Chromobacterium viscosum lipase showed the highest selectivity for the aza-Michael addition to substituted alkyl acrylates. For the first time also, some CLEAs were examined that showed a comparable or higher selectivity and yield than the free enzymes and other formulations.

Synthesis of 1-alkyl-2-(trifluoromethyl)azetidines and their regiospecific ring opening toward diverse α-(trifluoromethyl)amines via intermediate azetidinium salts

A convenient approach toward nonactivated 1-alkyl-2-(trifluoromethyl) azetidines as a new class of constrained azaheterocycles was developed starting from ethyl 4,4,4-trifluoroacetoacetate via imination, hydride reduction, chlorination, and base-induced ring closure. Furthermore, the reactivity profile of these 2-CF3-azetidines was assessed by means of quaternization and subsequent regiospecific ring opening at C4 of the azetidinium intermediates by oxygen, nitrogen, carbon, sulfur, and halogen nucleophiles, pointing to a clear difference in reactivity compared to azetidines bearing other types of electron-withdrawing groups at C2.

Graphene oxide: An efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes

Graphene oxide was found to be a highly efficient, reusable and cost-effective organocatalyst for the aza-Michael addition of amines to activated alkenes to furnish corresponding β-amino compounds in excellent yields. The Royal Society of Chemistry 2011.