105290-97-9

Basic information

• Product Name: Benzamide, N-[1-(2-methylphenyl)ethyl]-, (R)-
• CAS NO: 105290-97-9
• Molecular Formula: C16H17NO
• Molecular Weight: 239.317
• Mol File: 105290-97-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzamide, N-[1-(2-methylphenyl)ethyl]-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-[1-(2-methylphenyl)ethyl]-, (R)-(105290-97-9)
• EPA Substance Registry System: Benzamide, N-[1-(2-methylphenyl)ethyl]-, (R)-(105290-97-9)

Safety Data

• Hazardous Substances Data: 105290-97-9(Hazardous Substances Data)

Upstream product

• 577-16-2 2-Methylacetophenone 
• 105615-45-0 [(1R)-1-(2-methylphenyl)ethyl]amine 
• 98-88-4 benzoyl chloride 
• 42142-17-6 1-(o-tolyl)ethanamine 
• 93-97-0 benzoic acid anhydride 

Relevant articles and documents

Microwave-Enhanced Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl)imines

Microwave irradiation has considerably enhanced the efficiency of the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)imines in isopropyl alcohol catalyzed by a ruthenium complex bearing the achiral ligand 2-amino-2-methylpropan-1-ol. In addition to shortening reaction times for the transfer hydrogenation processes to only 30 min, the amounts of ruthenium catalyst and isopropyl alcohol can be considerably reduced in comparison with our previous procedure assisted by conventional heating, which diminishes the environmental impact of this new protocol. This methodology can be applied to aromatic, heteroaromatic and aliphatic N-(tert-butylsulfinyl)ketimines, leading, after desulfinylation, to the expected primary amines in excellent yields and with enantiomeric excesses of up to 96 %. Microwave irradiation promotes the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)imines in 2-propanol catalysed by a ruthenium complex bearing an achiral β-amino alcohol as ligand. After desulfinylation, α-branched primary amines containing aromatic, heteroaromatic and aliphatic substituents are obtained in excellent yields and with enantiomeric excesses of up to 96 %.

A versatile Ru catalyst for the asymmetric transfer hydrogenation of both aromatic and aliphatic sulfinylimines

A highly efficient Ru catalyst based on an achiral, very simple, and inexpensive amino alcohol ligand (2-amino-2-methylpropan-1-ol) has been developed for the asymmetric transfer hydrogenation (ATH) of chiral N-(tert-butylsulfinyl)imines. This complex is able to catalyze the ATH of both aromatic and the most challenging aliphatic sulfinylimines by using isopropyl alcohol as the hydrogen source. The diastereoselective reduction of aromatic, heteroaromatic, and aliphatic sulfinylketimines, including sterically congested cases, over short reaction times (1-4 h), followed by desulfinylation of the nitrogen atom, affords the corresponding highly enantiomerically enriched (ee up to >99%) α-branched primary amines in excellent yields. The same ligand was equally effective for the synthesis of both (R)- and (S)-amines by using the appropriate absolute configuration in the iminic substrate. DFT mechanistic studies show that the hydrogen-transfer process is stepwise. Moreover, the origin of the diastereoselectivity has been rationalized.