498542-97-5

Basic information

• Product Name: (1S,2S)-N-acetyl-N'-methyl-1,2-bis(trifluoromethanesulfonamido)cyclohexane
• Synonyms: (1S,2S)-N-acetyl-N'-methyl-1,2-bis(trifluoromethanesulfonamido)cyclohexane
• CAS NO: 498542-97-5
• Molecular Weight: 434.381
• Mol File: 498542-97-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1S,2S)-N-acetyl-N'-methyl-1,2-bis(trifluoromethanesulfonamido)cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-N-acetyl-N'-methyl-1,2-bis(trifluoromethanesulfonamido)cyclohexane(498542-97-5)
• EPA Substance Registry System: (1S,2S)-N-acetyl-N'-methyl-1,2-bis(trifluoromethanesulfonamido)cyclohexane(498542-97-5)

Safety Data

• Hazardous Substances Data: 498542-97-5(Hazardous Substances Data)

Upstream product

• 153077-87-3 C,C,C-trifluoro-N-(2-trifluoromethanesulfonylaminocyclohexyl)methanesulfonamide 
• 186581-53-3 diazomethane 
• 498542-91-9 (1S,2S)-N-acetyl-1,2-bis(trifluoromethanesulfonamido) cyclohexane 

Downstream Products

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 36283-44-0 N-acetyl-1-phenylethylamine 
• 19144-86-6 (S)-N-acetyl-1-phenylethylamine 

Relevant articles and documents

Tuning the enantioselective N-acetylation of racemic amines: A spectacular salt effect

We have described a spectacular salt effect in the kinetic resolution of (±)-1-phenylethylamine, which leads to an increase in reactivity, high levels of selectivity, and a complete reversal of the stereoselectivity. By tuning the reaction conditions, we

Kinetic resolution of amines: A highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity

Solvents lend a hand: Changing the polarity of the reaction solvent from 1,3-dimethyltetrahydropyrimidin-2-one (DMPU) to toluene reverses the stereo-selectivity observed in the acetylation of amines with (1S,2S)-1 (see scheme). Optimizing the reaction conditions led to an unprecedented 90% ee (S) in DMPU at -20°C with a 33% conversion.