173541-16-7

Basic information

• Product Name: (1'R)-1-(1'-phenylethyl)-1,5-dihydro-pyrrol-2-one
• Synonyms: (1'R)-1-(1'-phenylethyl)-1,5-dihydro-pyrrol-2-one
• CAS NO: 173541-16-7
• Molecular Weight: 187.241
• Mol File: 173541-16-7.mol

Chemical Properties

• CAS DataBase Reference: (1'R)-1-(1'-phenylethyl)-1,5-dihydro-pyrrol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1'R)-1-(1'-phenylethyl)-1,5-dihydro-pyrrol-2-one(173541-16-7)
• EPA Substance Registry System: (1'R)-1-(1'-phenylethyl)-1,5-dihydro-pyrrol-2-one(173541-16-7)

Safety Data

• Hazardous Substances Data: 173541-16-7(Hazardous Substances Data)

Upstream product

• 332-77-4 2,5-dihydro-2,5-dimethoxyfuran 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 96360-64-4 (1'R)-1-(1'-phenylethyl)-1H-pyrrole 

Downstream Products

• 173541-27-0 (1''R,2'R,4'S,5,5'R)-5-[4'-methyl-5'-phenyl-3'-(toluene-4'''-sulfonyl)oxazolidine-2'-yl]-1-(1''-phenylethyl)pyrrolidin-2-one 
• 173541-21-4 (1''R,2'R,4'S,5,5'R)-5-[4'-methyl-5'-phenyl-3'-(toluene-4'''-sulfonyl)oxazolidine-2'-yl]-1-(1''-phenylethyl)pyrrol-2-one 
• 173541-18-9 (1'R)-1-(1'-phenylethyl)-2-tert-butyldimethylsilyloxy-1H-pyrrole 

Relevant articles and documents

A new asymmetric approach towards 2-pyrrolidinones and pyrrolidines: Simple versus double stereodifferentiation

The condensation of a chiral 2-silyloxypyrrole derivative with achiral and chiral formyl cation equivalents has been studied for the first time. The methodology allows to build-up pyroglutammic aldehydes and prolinal systems with a stereocontrol from good to excellent. Whereas the chiral auxiliary residing on the pyrrole system shows an intrinsic good level of diastereoface discrimination at C-5, the combined use of a 2-methoxy-3-tosyl-oxazolidine as a chiral formylating agent allows a total stereocontrol of the condensation. A rationale for the observed stereochemical outcome is presented.

A new asymmetric approach toward 5-substituted pyrrolidin-2-one derivatives

The condensation between a chiral 2-silyloxypyrrole and either achiral or chiral formyl cation equivalents has been studied. The methodology has allowed to build-up 5-substituted pyrrolidin-2-one derivatives with a stereocontrol from good to excellent. The chiral auxiliary located on the silyloxypyrrole showed an intrinsic good level of diastereoface discrimination at C-5. However, the use of a 2-methoxy-3-tosyl-oxazolidine as chiral formylating agent allowed a total stereocontrol in the condensation. A rationale for the observed stereochemical outcome is presented. The stereoselective manipulation of these adducts provided new potentially interesting pyroglutamic aldehyde and prolinal derivatives, whereas treatment with TiCl4 triggered unexpectedly a Pomeranz-Fritsch type intramolecular condensation affording a benzocondensated indolizidinone.