56875-02-6

Usage

InChI:InChI=1/C6H13NO2/c1-5(2)4-7-6(8)9-3/h5H,4H2,1-3H3,(H,7,8)

Upstream product

• 78-81-9 isobutylamine 
• 79-22-1 methyl chloroformate 
• 616-38-6 carbonic acid dimethyl ester 
• 105941-73-9 (2-Methyl-3-tributylstannanyl-propyl)-carbamic acid methyl ester 

Downstream Products

• 78999-71-0 (2-Methyl-1-phenylcarbamoyl-propyl)-carbamic acid methyl ester 
• 189624-13-3 N-methoxycarbonyl-2-hydroxy-2-methylpropylamine 
• 68723-28-4 N-methyl-N-benzylisobutylamine 

Relevant academic research and scientific papers

Sc(OTf)3-catalyzed carbomethoxylation of aliphatic amines with dimethyl carbonate (DMC): DMC activation by η1-O(C{double bond, long}O) coordination to Sc(III) and its relevance to catalysis

The role of metal center in the Sc(OTf)3-catalyzed carbomethoxylation of aliphatic amines with DMC has been investigated. We have shown that the catalytic formation of carbamate ester is promoted by coordination of DMC to scandium(III) ion through the carbonyl oxygen atom. The ability of DMC to coordinate to Sc(III) has been proved by IR and NMR spectroscopy and fully demonstrated also by the isolation, for the first time, of a DMC-metal complex characterized as (η1-O(C{double bond, long}O)-DMC)Sc(OTf)3. A relationship has been shown between the coordination mode of DMC to Sc(III) and the reactivity of coordinated organic carbonate: coordination of DMC to Sc(III) activates both carbonyl group and O-CH3 moieties of the carbonic acid diester and enhances not only the carbomethoxylating but also the methylating activity of the ambident electrophile (DMC), as documented by the different selectivity exhibited by the catalyst in the aminolysis reaction of DMC with benzylamine and aniline, respectively.

Group 3 metal (Sc, La) triflates as catalysts for the carbomethoxylation of aliphatic amines with dimethylcarbonate under mild conditions

The activity of Sc(OTf)3 and La(OTf)3 (OTf=SO 3CF3) as catalysts for the phosgene-free synthesis of carbamate esters via carbomethoxylation of aliphatic amines with dimethylcarbonate (DMC) has been investigated. In the presence of M(OTf) 3 (M=Sc, La), primary and secondary aliphatic amines easily react with dimethylcarbonate, under very mild conditions (20°C), to afford carbamate esters with good yield and excellent selectivity (?100%). Sc(OTf)3 is a more effective catalyst than the homologue La salt. The carbomethoxylation reaction requires as strict anhydrous conditions, as, at 20°C, the presence of water inhibits markedly the catalytic activity of both triflate salts. Temperature influences carbamate selectivity, which is lower at higher temperature because of deleterious formation of N-methylation side-products.

CHELATION ASSISTED TRANSMETALLATION OF TETRAALKYL TIN DERIVATIVES: C-METALLATED LITHIOCARBAMATES AS d3 REAGENTS FOR THE SYNTHESIS OF δ-HYDROXYCARBAMATES.

The γ-stannylcarbamates 4 and 5 were subjected to metallation with two equivalents of BuLi to give the dianions 6 and 7 acting as d3 reagents.The C-metallation involves a chelation assisted transmetallation.