24211-54-9

Basic information

• Product Name: (S)-5-HYDROXY-PIPERIDIN-2-ONE
• Synonyms: RARECHEM AK ML 0202;(S)-5-HYDROXY-PIPERIDIN-2-ONE;2-Piperidinone, 5-hydroxy-, (5S)-;(S)-5-Hydroxy-2-piperidinone;(-)-(5S)-5-hydroxy-piperidin-2-one
• CAS NO: 24211-54-9
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• Product Categories: pharmacetical
• Mol File: 24211-54-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 123-124℃ (methanol ethyl ether )
• Boiling Point: 352.263 °C at 760 mmHg
• Flash Point: 166.843 °C
• Appearance: /
• Density: 1.2 g/cm³
• Storage Temp.: 2-8°C
• PKA: 14.21±0.20(Predicted)
• CAS DataBase Reference: (S)-5-HYDROXY-PIPERIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-HYDROXY-PIPERIDIN-2-ONE(24211-54-9)
• EPA Substance Registry System: (S)-5-HYDROXY-PIPERIDIN-2-ONE(24211-54-9)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 24211-54-9(Hazardous Substances Data)

Usage

Uses

(5S)-5-Hydroxy-2-piperidinone is used in the enantioselective synthesis of peptides containing cyclopropane pipecolic acid, which can be useful as proline mimetics for probing protein-ligand interactions and generating novel bioactive compounds.

Upstream product

• 24211-53-8 (S)-(+)-5-Azidomethyl-2-oxotetrahydrofuran 
• 76543-09-4 methyl 3-(oxiran-2-yl)propanoate 
• 1729-32-4 5-iodomethyl-dihydro-furan-2-one 
• 591-80-0 pent-4-enoic acid 
• 58960-19-3 2-{[5-oxotetrahydrofuran-2-yl]methyl}-1H-isoindole-1,3(2H)-dione 
• 1179999-39-3 methyl 4-hydroxy-5-nitropentanoate 
• 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

• 176966-76-0 (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one 
• 24211-55-0 (S)-3-hydroxypiperidine 

Relevant articles and documents

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).

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.

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.