24211-54-9

Usage

Uses

Used in Pharmaceutical and Biochemical Research:
(S)-5-HYDROXY-PIPERIDIN-2-ONE is used as a key intermediate in the enantioselective synthesis of peptides containing cyclopropane pipecolic acid. These peptides are valuable as proline mimetics, which can be utilized for probing protein-ligand interactions. This application is crucial in understanding the binding mechanisms of various proteins, leading to the development of novel bioactive compounds with potential therapeutic applications.

Upstream product

• 24211-53-8 (S)-(+)-5-Azidomethyl-2-oxotetrahydrofuran 
• 1179999-39-3 methyl 4-hydroxy-5-nitropentanoate 
• 58960-19-3 2-{[5-oxotetrahydrofuran-2-yl]methyl}-1H-isoindole-1,3(2H)-dione 
• 591-80-0 pent-4-enoic acid 
• 1729-32-4 5-iodomethyl-dihydro-furan-2-one 
• 76543-09-4 methyl 3-(oxiran-2-yl)propanoate 
• 102774-93-6 (S)-(5-oxotetrahydrofuran-2-yl)methyl methanesulfonate 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 58879-34-8 (S)-5-tosyloxypentan-4-olide 

Downstream Products

• 24211-55-0 (S)-3-hydroxypiperidine 
• 87179-79-1 (S)-1-benzyl-5-(benzyloxy)piperidin-2-one 
• 176966-76-0 (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one 
• 1259404-17-5 tasocitinib 
• 477600-74-1 tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate 

Relevant academic research and scientific papers

Concise Enantioselective Synthesis of Naturally Active (S)-3-Hydroxypiperidine

A short and efficient enantioselective synthesis of natural product (S)-3-hydroxypiperidine has been achieved starting from commercially available raw materials employing two catalytic routes: (i) cocatalyzed hydrolytic kinetic resolution (HKR) of racemic methyl-3-(oxiran-2-yl)propanoate; (ii) proline-catalyzed α-aminooxylation followed by Horner-Wardsworth-Emmons olefination in high enantiomeric purity (97% ee) and high overall yield (38%). (Chemical Equation Presented).

A practical and enantiospecific synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ols

A highly enantiospecific, azide-free synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ol in excellent yield was developed. The key step of the synthesis involves the enantiospecific ring openings of enantiomerically pure (R)- and (S)-2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-diones with the diethyl malonate anion and subsequent decarboxylation.

Asymmetrie copper(l)-catalyzed Henry reaction with an aminoindanol-derived bisoxazolidine ligand

Bisoxazolidine 1 Is an effective ligand In the Me2Zn-promoted and the Cu(l)-catalyzed Henry reaction. While a wide range of nitroaldol products are obtained In high yields and ee's In both cases, the replacement of dimethylzinc with copper(l) acetate results In a complete reversal of the sense of asymmetric Induction. The Cu(l)-catalyzed enantioselective addition of nitromethane to methyl 4-oxobutanoate followed by hydrogenation and spontaneous lactamlzatlon gives (S)-5-hydroxyplperldln-2-one In 72% overall yield and 98% ee which compares favorably with previously reported methods.

Microwave-enhanced hydrogenations at medium pressure using a newly constructed reactor

The newly constructed reactor for hydrogenations in microwave fields allows to work out the syntheses up to 25 bar. This is shown for the synthesis of intermediates of active agents. In order to demonstrate the superiority of the microwave-assisted hydrogenation, the reactions are compared with classical hydrogenations. The following reactions were carried out: dearomatization, debenzylation, azide hydrogenation and the hydrogenation of strychnine.

Synthesis of carbohydrate-based monomers that are precursors for the preparation of stereoregular polyamides

The syntheses of some derivatives of 5-amino-5-deoxy-L-arabinonic acid, 5- amino-5-deoxy-D-xylonic acid and (S)-5-amino-4-hydroxypentanoic acid have been performed in several steps from L-arabinose, D-xylose and (S)-(+)- glutamic acid, respectively. These ω-aminoacids are precursors of bifunctional monomers that could be used for the preparation of optically active polyamides.

Enantioenriched N-(2-Chloroalkyl)-3-acetoxypiperidines as Potential Cholinotoxic Agents. Synthesis and Preliminary Evidence for Spirocyclic Aziridinium Formation.

The syntheses of six enantioenriched analogs representing cyclic forms of acetylcholine are reported. (S)- and (R)-N-(2-chloroethyl)-3-acetoxypiperidine and (R,R)-, (R,S)-, (S,R)-, and (S,S)-N-(2-chloropropyl)-3-acetoxypiperidine have been synthesized from (R)- or (S)-3-hydroxypiperidine in five steps. (R)- and (S)-3-hydroxypiperidine were accessed via parallel stereospecific routes from d- and l-glutamic acid, and through fractional recrystallization of diastereomeric tartranilic acid salts. (S)-N-(2-Chloroethyl)-3-acetoxypiperidine was reacted with silver perchlorate to form a spirocyclic aziridinium analog of acetylcholine as evidenced by a characteristic 1H NMR shift for the aziridinium methylene groups.