187091-61-8

Upstream product

• 129823-21-8 (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione 
• 100-39-0 benzyl bromide 
• 192987-92-1 (-)-(4S,5R)-1-benzyl-4-benzyloxy-5-hydroxy-2-pyrrolidinone 
• 170711-05-4 (S)-1-benzyl-3-(benzyloxy)pyrrolidine-2,5-dione 
• 75-16-1 methylmagnesium bromide 
• 170711-09-8 (-)-(4S,5R)-1-benzyl-4-benzyloxy-5-sulfonyl-2-pyrrolidinone 
• 187091-54-9 (S)-1-Benzyl-4-benzyloxy-5-hydroxy-5-methyl-pyrrolidin-2-one 
• 101469-91-4 (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 

Downstream Products

• 187091-63-0 (+)-(4S,5R)-1-benzyl-4-hydroxy-5-methyl-2-pyrrolidinone 
• 187091-66-3 (-)-(2R,3S)-3-azido-1-benzyl-2-methylpyrrolidine 
• 187091-65-2 Methanesulfonic acid (2R,3S)-1-benzyl-2-methyl-pyrrolidin-3-yl ester 
• 187091-67-4 (-)-(2R,3R)-1-benzyl-2-methylpyrrolidin-3-amine 
• 187091-64-1 (-)-(2R,3S)-1-benzyl-3-hydroxy-2-methylpyrrolidine 

Relevant academic research and scientific papers

A flexible approach to protected (4S,5S)-5-alkyl-1-benzyl-4-benzyloxy-2- pyrrolidinones

We report in this paper a flexible approach to (4S,5S)-5-alkyl-1-benzyl-4- benzyloxy-2-pyrrolidinones 7 starting from the known 5-alkyl-1-benzyl-4- benzyloxy-5-hydroxy-2-pyrrolidinones 6. The method is based on TMSCl-mediated reductive dehydroxylation of 6 with Zn(BH4)2, which allows the synthesis of a variety of 2-pyrrolidinones 7 in 48-75% yields with cis=trans diastereoselectivities ranging from 58:42 to 90:10. Copyright

An alternative stereoselective synthesis of protected trans-5-alkyl-4- hydroxy-2-pyrrolidinones

A flexible approach to protected trans-5-alkyl-4-hydroxy-2- pyrrolidinones was described. The key step involved the α-amidoalkylation of benzenesulfone derived from (S)-malic acid, with organozinc reagents generated in situ from Grignard reagents and anhydrous ZnCl2·OEt2.

An easy access to protected (4S, 5R)-5-alkyl-4-hydroxy-2-pyrrolidinones and their use as versatile synthetic intermediates

A versatile approach to enantiopure (4S, 5R)-5-alkyl-4-hydroxy-2- pyrrolidinones is described. The key steps involve a regioselective Grignard reagent addition to (S)-malimides, and diastereoselective reductive dehydroxylation of the resulting hemi-azaketals. The flexibility of this methodology has been demonstrated by the synthesis of (2R, 3R)-3-amino-1- benzyl-2-methylpyrrolidine, the parent diamine of antipsychotic agent, emonapride, and the unnatural enantiomer of the β-hydroxy-γ-amino acid residue of hapalosin in lactam form.

First asymmetric synthesis of (2R,3R)-3-amino-1-benzyl-2-methylpyrrolidine via a highly diastereoselective reductive alkylation

The first asymmetric synthesis of (2R,3R)-3-amino-1-benzyl-2-methylpyrrolidine, the parent diamine of antipsychotic agent, emonapride, from (S)-malic acid was achieved via a highly diastereoselective reductive alkylation.