178320-64-4

Basic information

• Product Name: Trifluoro-methanesulfonic acid 5-ethoxy-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester
• Synonyms: Trifluoro-methanesulfonic acid 5-ethoxy-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester
• CAS NO: 178320-64-4
• Molecular Weight: 415.411
• Mol File: 178320-64-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Trifluoro-methanesulfonic acid 5-ethoxy-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Trifluoro-methanesulfonic acid 5-ethoxy-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester(178320-64-4)
• EPA Substance Registry System: Trifluoro-methanesulfonic acid 5-ethoxy-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester(178320-64-4)

Safety Data

• Hazardous Substances Data: 178320-64-4(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 39662-63-0 5-ethoxy-pyrrolidin-2-one 
• 111711-61-6 5-ethoxy-1-p-toluenesulfonyl-2-pyrrolidinone 
• 145100-51-2 N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 178320-70-2 5-Ethoxy-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester 
• 178320-65-5 2-Ethoxy-1-(toluene-4-sulfonyl)-5-vinyl-2,3-dihydro-1H-pyrrole 

Relevant articles and documents

Synthesis and Further Reactivity of Functionalized Lactam-Derived Enol Triflates

Pyrrolidinone- and piperidinone-derived enol triflates 2 were prepared in high yield (60-97%) from the corresponding lactams 1 using KHMDS and N-(5-chloro-2-pyridyl)triflimide. A structure-stability study on the less stable pyrrolidinone-derived triflates revealed that an N-tosyl group is essential, and an α-ethoxy substituent enhances thermal stability. Substituents at the 3- and 4-position are tolerated. Substitution of the triflate moiety by a wide variety of functional groups was achieved under mild conditions via metal-mediated reactions. Although cuprate couplings proceeded in only moderate yields, several palladium-catalyzed reactions gave good yields of interesting molecules for further synthetic operations (for example, Stille coupling with vinylstannanes, cross-coupling with arylzincs, and carbonylation processes). Preparation of the first enantiopure lactam-derived enol triflate 15 (from (S)-pyroglutamic acid) is described. Enamide hydrogenation of derivative 17 allowed the synthesis of a proline analogue 18 in excellent yield and diastereoselectivity (86% de). ? Abstract published in Advance ACS Abstracts, October 15, 1997.

Synthesis and reactivity of pyrrolidinone- and piperidinone-derived enol triflates

A high yielding route to cyclic lactam-derived enol triflates is given along with a study of the structural features necessary for such triflates to be of useful thermal stability. Some Pd(0)-mediated coupling reactions are disclosed as well as the first