158249-50-4

Basic information

• Product Name: (4R)-4-Butyl-2-oxazolidinone
• Synonyms: (4R)-4-Butyl-2-oxazolidinone
• CAS NO: 158249-50-4
• Molecular Formula: C7H13NO2
• Molecular Weight: 143.18362
• Mol File: 158249-50-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 310.4±9.0 °C(Predicted)
• Appearance: /
• Density: 1.002±0.06 g/cm3(Predicted)
• PKA: 12.84±0.40(Predicted)
• CAS DataBase Reference: (4R)-4-Butyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-4-Butyl-2-oxazolidinone(158249-50-4)
• EPA Substance Registry System: (4R)-4-Butyl-2-oxazolidinone(158249-50-4)

Safety Data

• Hazardous Substances Data: 158249-50-4(Hazardous Substances Data)

Usage

General Description

(4R)-4-Butyl-2-oxazolidinone is a chemical compound with the molecular formula C8H15NO2. It is a chiral oxazolidinone derivative, with a four-carbon butyl group attached to the nitrogen atom. (4R)-4-Butyl-2-oxazolidinone is commonly used as a synthetic intermediate in the production of pharmaceuticals and agrochemicals. It has been found to exhibit antibacterial and antifungal activity, making it a potential candidate for the development of new antimicrobial agents. Additionally, (4R)-4-Butyl-2-oxazolidinone has also been studied for its potential use in the synthesis of chiral ligands and catalysts in organic chemistry. Overall, (4R)-4-Butyl-2-oxazolidinone is a versatile chemical with various applications in the field of organic synthesis and pharmaceutical research.

Upstream product

• 227079-42-7 (R)-2-Ethoxycarbonylaminohexanol 
• 155398-62-2 (4S)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-oxazolidin-2-one 
• 227079-43-8 (R)-2-Ethoxycarbonylaminohexyl methanesulfonate 
• 2417-93-8 propyllithium 
• 154669-49-5 [(S)-2-oxooxazolidin-4-yl]methyl-4-methylbenzenesulfonate 

Relevant articles and documents

Synthesis of N-protected 2-aminohexanesulfonic acid

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Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion

Chiral β-amino alcohols are important building blocks for the synthesis of drugs, natural products, chiral auxiliaries, chiral ligands and chiral organocatalysts. The catalytic asymmetric β-amination of alcohols offers a direct strategy to access this class of molecules. Herein, we report a general intramolecular C(sp3)-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors of chiral β-amino alcohols. Specifically, the ring-closing C(sp3)-H amination of N-benzoyloxycarbamates with 2 mol% of a chiral ruthenium catalyst provides cyclic carbamates in up to 99% yield and with up to 99% ee. The method is applicable to benzylic, allylic, and propargylic C-H bonds and can even be applied to completely non-activated C (sp3)-H bonds, although with somewhat reduced yields and stereoselectivities. The obtained cyclic carbamates can subsequently be hydrolyzed to obtain chiral β-amino alcohols. The method is very practical as the catalyst can be easily synthesized on a gram scale and can be recycled after the reaction for further use. The synthetic value of the new method is demonstrated with the asymmetric synthesis of a chiral oxazolidin-2-one as intermediate for the synthesis of the natural product aurantioclavine and chiral β-amino alcohols that are intermediates for the synthesis of chiral amino acids, indane-derived chiral Box-ligands, and the natural products dihydrohamacanthin A and dragmacidin A.[Figure not available: see fulltext.].

A new route for protected amino alcohols from (R)-glycidol. Copper(I) mediated alkylation of 4-tosyloxymethyl-2-oxazolidinone

The reaction of (S)-4-tosyloxymethyl-2-oxazolidinone, which was synthesized from (R)-glycidol through (R)-4-benzoyloxymethyl-2-oxazolidinone, with various lithium dialkylcuprate(I)s in THF proceeded smoothly to afford the corresponding protected amino alcohol derivatives in good yield.