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Usage

Uses

Used in Pharmaceutical Synthesis:
Benzyl-(1-amino-3-chloro-2-propanol) is utilized as a chiral auxiliary in the synthesis of pharmaceuticals, contributing to the production of enantiomerically pure compounds, which is crucial for ensuring the desired biological activity and minimizing potential side effects.
Used in Organic Compounds Synthesis:
benzyl-(1-amino-3-chloro-2-propanol) also serves as a building block in the synthesis of various organic compounds, facilitating the creation of complex molecular structures with specific stereochemistry.
Used in Antimicrobial Applications:
Due to its antimicrobial properties, benzyl-(1-amino-3-chloro-2-propanol) is employed in applications aimed at inhibiting the growth of harmful microorganisms, which can be beneficial in medical, industrial, and environmental contexts.
Used in Antiviral Applications:
The antiviral characteristics of benzyl-(1-amino-3-chloro-2-propanol) make it a potential candidate for the development of treatments against viral infections, offering a new avenue for therapeutic intervention.
Used in Antitumor Applications:
Its antitumor properties position benzyl-(1-amino-3-chloro-2-propanol) as a component in the development of cancer therapies, potentially contributing to the inhibition of tumor growth and the advancement of novel treatment strategies.
Used in Material Development:
benzyl-(1-amino-3-chloro-2-propanol)'s potential applications extend to the development of new materials, where its unique structural features may impart specific properties to the materials, such as improved stability or reactivity.
Used in Organic Chemistry Reactions:
Benzyl-(1-amino-3-chloro-2-propanol) also functions as a reagent in organic chemistry reactions, where it can facilitate or enhance the synthesis of target molecules, contributing to the advancement of chemical research and the discovery of new compounds.

InChI:InChI=1/C10H14ClNO/c11-6-10(13)8-12-7-9-4-2-1-3-5-9/h1-5,10,12-13H,6-8H2

Upstream product

• 100-46-9 benzylamine 
• 106-89-8 epichlorohydrin 

Downstream Products

• 111043-42-6 N-benzyl-3-(trimethylsilyloxy)azetidine 
• 111043-32-4 1-benzyl-(3-chloro-2-trimethylsilyloxypropyl)-amine 
• 143759-64-2 1-[4,4-Bis(4-fluorophenyl)butyl]-4-(2-hydroxy-3-phenylmethylaminopropyl)piperazine 
• 54881-13-9 N-benzyl-3-hydroxyazetidine 
• 56862-39-6 3-(N-benzyl-N-methyl)amino-2-chloro-1-propene 
• 685891-48-9 1-benzyl-3-chloroazetidine 
• 1218777-31-1 C₁₁H₁₄N₂O₂ 
• 1229358-21-7 C₁₅H₂₂ClNO₃ 
• 80236-09-5 N-benzyl-1-(oxiran-2-yl)methanamine 
• 223382-13-6 1-benzylazetidine-3-ol hydrochloride 
• 66434-74-0 N-benzyl-5-hydroxyoxazinan-2-one 
• 107835-88-1 (RS)-3-benzyl-5-(hydroxymethyl)-1,3-oxazolidin-2-one 
• 156303-83-2 1-benzyl-3-azetidinone 
• 67160-49-0 1-benzyl-3-methanesulfonyloxyazetidine 

Relevant academic research and scientific papers

Green Regio- and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent-Free Conditions

The ring-opening reactions of epoxides with amines were efficiently and regioselectively catalyzed by high-surface-area graphite and graphene oxide under metal-free and solvent-free conditions. For epoxides without aryl groups, catalytic activity was observed only for graphene oxide, and hence, the activity must have been due to its acidic groups. For styrene oxide, instead, graphite and graphene oxide exhibited rather similar catalytic activities, and hence, the activity was mainly due to activation of the electrophilic epoxide by π-stacking interactions with the graphitic π system. The described aminolysis procedure is green and cheap because the catalyst can be recovered and recycled without loss of efficiency. Moreover, these heterogeneous catalysts exert high stereoselective control in the presence of nonracemic epoxides and provide chiral β-amino alcohols with enantiomeric excess values up to 99 %.

Development of an optimized process for the preparation of 1-benzylazetidin-3-ol: An industrially important intermediate for substituted azetidine

A thoroughly optimized and robust process for the synthesis of 1-benzylazetidin-3-ol has been emphasized. 1-Benzylazetidin-3-ol has been utilized as a starting material in the commercial synthesis of azetidin-3-ol hydrochloride. Synthesis of azetidin-3-ol hydrochloride involves the usage of very low cost and commercially available starting material (benzylamine) and with reduced formation of di(3-chloro-2-hydroxypropyl) benzylamine significantly resulting in an economical process that allows the effective production of 1-benzyl azetidin-3-ol as well as azetidin-3-ol hydrochloride.

Highly regioselective and efficient synthesis of aminoepoxides by ring closure of aminohalohydrins mediated by KF-Celite

The regioselective synthesis of several aminoepoxides has been achieved without observing any trace of azetidinols, which are usually reported as the exclusive reaction products when aminohalohydrins are treated with bases. The use of the mild supported base KF-Celite in refluxing acetonitrile is crucial for modulating the excellent regioselectivity observed. Georg Thieme Verlag Stuttgart . New York.

Seebach's conjunctive reagent enables double cyclizations

(Figure presented) When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein.

DMAP-catalyzed synthesis of 2-oxazolidinones from corresponding halohydrins using KOCN/DMF

We report facile and simple synthesis of a variety of 2-oxazolidinones from the corresponding halohydrins by reaction with KOCN in DMF catalyzed by DMAP. DMAP and temperature play key roles in enriching the yield of 2-oxazolidinones. A few examples in this Letter are applicable to pharmaceutically important processes.

Catalyst-free process for the synthesis of 5-aryl-2-oxazolidinones via cycloaddition reaction of aziridines and carbon dioxide

A simple approach for facile synthesis of 5-aryl-2-oxazolidinones in excellent regioselectivity from aziridines under compressed CO2 conditions was developed in the absence of any catalyst and organic solvent. The reaction outcome was found to be tuned by subtly adjusting CO2 pressure. The adduct formed in situ of aziridine and CO2 is assumed to act as a catalyst in this reaction, which was also studied by means of in situ FT-IR technique.

ACID ADDITION SALTS OF SYNTHETIC INTERMEDIATES FOR CARBAPENEM ANTIBIOTICS AND PROCESSES FOR PREPARING THE SAME

The present invention provides a process for preparing an acid addition salt of a synthetic intermediate for carbapenem antibiotics and a novel acid addition salt of a synthetic intermediate for carbapenem antibiotics obtained from the process. The present invention also provides a process for preparing a carbapenem antibiotic using the acid addition salt. According to the process of the present invention, an acid addition salt of a synthetic intermediate for carbapenem antibiotics can be prepared in a high yield and high purity, without conducting column chromatography. Thus, the process of the present invention can be applied to mass production with an industrial scale. Furthermore, since the acid addition salts have solid forms, they are easy to handle and keep in a manufacturing site.

ACID ADDITION SALTS OF SYNTHETIC INTERMEDIATES FOR CARBAPENEM ANTIBIOTICS AND PROCESSES FOR PREPARING THE SAME

The present invention provides a process for preparing an acid addition salt of a synthetic intermediate for carbapenem antibiotics and a novel acid addition salt of a synthetic intermediate for carbapenem antibiotics obtained from the process. The present invention also provides a process for preparing a carbapenem antibiotic using the acid addition salt. According to the process of the present invention, an acid addition salt of a synthetic intermediate for carbapenem antibiotics can be prepared in a high yield and high purity, without conducting column chromatography. Thus, the process of the present invention can be applied to mass production with an industrial scale. Furthermore, since the acid addition salts have solid forms, they are easy to handle and keep in a manufacturing site.

A practical and facile synthesis of azetidine derivatives for oral carbapenem, L-084

An orally active carbapenem L-084, which exhibits high bioavailability in humans, has a 1-(1,3-thiazolin-2-yl)azetidin-3-ylthio moiety at the C-2 position of the 1β-methylcarbapenem skeleton. We established a practical and cost-effective synthesis of 3-mercapto-1-(1,3-thiazolin-2-yl)azetidine (1) for further scale-up production of L-084. This synthesis method entails an industry-oriented reaction of azetidine ring-closure to yield N-benzyl-3-hydroxyazetidine (16), which is eventually converted to 1 via key intermediates, Bunte salts 19 and 20.

2-ARYLMETHYLAZETIDINE CARBAPENEM DERIVATIVES AND PREPARATION THEREOF

A 2-arylmethylazetidine carbapenem derivative of formula ( I ) or a pharmaceutically acceptable salt thereof exhibits a wide spectrum of antibacterial activities against Gram-positive and Gram-negative bacteria and excellent antibacterial activities against resistant bacteria such as methicillin-resistant Staphylococcus aureus (MRSA) and quinolone-resistant strains (QRS).