169221-13-0

Upstream product

• 70006-37-0 rac-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone 
• 169221-12-9 (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone 
• 76-86-8 Triphenylsilyl chloride 
• 79-50-5 pantolactone 
• 62-53-3 aniline 
• 750649-50-4 (R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 3-(4-chlorophenyl)-2-propenoate 
• 750649-46-8 (3R,3'R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 4-nitro-3-(4-chlorophenyl)butanoate 
• 674776-35-3 (3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl (2R)-3-cyano-2-(4-isobutylphenyl)propionate 
• 247248-94-8 4,4-dimethyl-1-phenylpyrrolidine-2,3-dione 

Downstream Products

• 226387-97-9 (αS,3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl α-phthalimidopropanoate 
• 496785-30-9 (αR,3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl α-phthalimidopropanoate 
• 496785-33-2 (αR,3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl α-phthalimido-β-phenylpropanoate 
• 496785-33-2 (αS,3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl α-phthalimido-β-phenylpropanoate 

Relevant academic research and scientific papers

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.

A synthesis of levetiracetam based on (S)-N-phenylpantolactam as a chiral auxiliary

The synthesis of levetiracetam and its enantiomer by deracemization of (±)-2-bromobutyric acid using either (S)- or (R)-N-phenylpantolactam as chiral auxiliaries, followed by SN2 substitution of the bromine atom by a 2-oxopyrrolidin-1-yl group and amidation of the carboxylic acid, is described.

Stereoselective synthesis of both enantiomers of N-Boc-α-aryl- γ-aminobutyric acids

Esterification of racemic α-aryl-β-cyanopropionic acid chlorides with either (R)- or (S)-N-phenylpantolactam as the chiral auxiliary in the presence of Et3N resulted in the predominant formation of (αR,3′R)- or (αS,3′S)-configured pantolactam c

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.

(R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone by lipase-catalyzed resolution of the racemic mixture: New chiral auxiliaries related to pantolactone

(R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone (R)- and (S)-1 have been prepared by lipase-catalyzed enantioselective acetylation of (S)-1 from rac-1 with vinyl acetate. Controlled hydrolysis of the acetate (S)-2 gave (S)-1. The configuration of (R)-1 and its p-bromobenzoate (R)-3 were established by X-ray diffraction analysis.