169221-12-9

Basic information

• Product Name: 2-Pyrrolidinone, 3-hydroxy-4,4-dimethyl-1-phenyl-, (3S)-
• CAS NO: 169221-12-9
• Molecular Formula: C12H15NO2
• Molecular Weight: 205.257
• Mol File: 169221-12-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-Pyrrolidinone, 3-hydroxy-4,4-dimethyl-1-phenyl-, (3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinone, 3-hydroxy-4,4-dimethyl-1-phenyl-, (3S)-(169221-12-9)
• EPA Substance Registry System: 2-Pyrrolidinone, 3-hydroxy-4,4-dimethyl-1-phenyl-, (3S)-(169221-12-9)

Safety Data

• Hazardous Substances Data: 169221-12-9(Hazardous Substances Data)

Upstream product

• 70006-37-0 rac-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone 
• 76-86-8 Triphenylsilyl chloride 
• 79-50-5 pantolactone 
• 62-53-3 aniline 
• 873786-88-0 (αR,3S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 2-(2-oxopyrrolidin-1-yl)butyrate 
• 873786-87-9 (αS,3S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 2-(2-oxopyrrolidin-1-yl)butyrate 
• 750649-48-0 (3S,3'S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 4-nitro-3-(4-chlorophenyl)butanoate 
• 247248-94-8 4,4-dimethyl-1-phenylpyrrolidine-2,3-dione 
• 615252-88-5 (S)-3-acetoxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone 

Downstream Products

• 252638-29-2 (S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl acrylate 
• 873786-87-9 (αS,3S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 2-(2-oxopyrrolidin-1-yl)butyrate 
• 873786-88-0 (αR,3S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 2-(2-oxopyrrolidin-1-yl)butyrate 
• 252638-35-0 (11R,3'S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 9,10-dihydro-9,10-ethanoanthracene-11-carboxylate 
• 252638-33-8 (1S,2S,3'S,4S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl bicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 252638-34-9 (1R,3'S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 4-methylcyclohex-3-enecarboxylate 
• 674776-35-3 (3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl (2R)-3-cyano-2-(4-isobutylphenyl)propionate 
• 674776-34-2 (3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl (2R)-3-cyano-2-phenylpropionate 
• 169221-13-0 (R)-3-hydroxy-4,4-dimethyl-1-phenylpyrrolidin-2-one 
• 750649-48-0 (3S,3'S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 4-nitro-3-(4-chlorophenyl)butanoate 

Relevant articles and documents

Silylation-based kinetic resolution of α-hydroxy lactones and lactams

A silylation-based kinetic resolution has been developed for α-hydroxy lactones and lactams employing the chiral isothiourea catalyst (-)-benzotetramisole and triphenylsilyl chloride as the silyl source. The system is more selective for lactones than lactams, and selectivity factors up to 100 can be achieved utilizing commercially available reagents.

Synthesis of both enantiomers of baclofen using (R)- and (S)-N-phenylpantolactam as chiral auxiliaries

Esterification of racemic 4-nitro-3-(4-chlorophenyl)butanoic acid with (R)- or (S)-N-phenylpantolactam as the chiral auxiliary allowed us to obtain the (3R,3′R)- or (3S,3′S)-nitro esters with >98:2 dr after column chromatography. Hydrolysis of the resulti

Enantioselective synthesis of both enantiomers of 3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone

The chiral auxiliaries (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone were obtained in good yield and e.e. by enantioselective reduction of 4,4-dimethyl-1-phenylpyrrolidine-2,3-dione with (-)- and (+)-B-chlorodiisopinocamphenylborane, (-)- and (+)-DIP-Chloride, respectively. The (R)-enantiomer was also obtained by enantioselective hydrogenation of the same precursor using a complex of 1,5-cyclooctadiene Rh(I) and (2S,4S)-1-(tert-butoxycarbonyl)-4-(diphenylphosphino)-2-(diphenylphosphinomethyl )pyrrolidine, (S,S)-BPPM, as the chiral catalyst.