(S)-5-Hydroxypiperidin-2-one

Base Information

• Chemical Name: (S)-5-Hydroxypiperidin-2-one
• CAS No.: 24211-54-9
• Molecular Formula: C5H9NO2
• Molecular Weight: 115.132
• Hs Code.: 2933790090
• European Community (EC) Number: 801-035-1
• DSSTox Substance ID: DTXSID80449933
• Nikkaji Number: J975.669H
• Wikidata: Q72481320
• Mol file: 24211-54-9.mol

Synonyms:(S)-5-Hydroxypiperidin-2-one;24211-54-9;(S)-5-Hydroxy-piperidin-2-one;(5S)-5-hydroxypiperidin-2-one;(S)-5-HYDROXY-2-PIPERIDINONE;2-Piperidinone, 5-hydroxy-, (5S)-;MFCD06202374;(s)-5-hydroxy-2-piperidone;5alpha-Hydroxypiperidine-2-one;SCHEMBL1559273;DTXSID80449933;GPRZVNYVEZZOKH-BYPYZUCNSA-N;CS-D0042;AKOS006295749;AM84823;AS-37856;(S)-5-hydroxy-piperidin-2-one, AldrichCPR;A848713;5-Hydroxy-piperidin-2-one

Chemical Property of (S)-5-Hydroxypiperidin-2-one

Chemical Property:

• Melting Point: 123-124℃ (methanol ethyl ether )
• Boiling Point: 352.263 °C at 760 mmHg
• PKA: 14.21±0.20(Predicted)
• Flash Point: 166.843 °C
• PSA: 49.33000
• Density: 1.2 g/cm³
• LogP: -0.41390
• Storage Temp.: 2-8°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 115.063328530
• Heavy Atom Count: 8
• Complexity: 103

Purity/Quality:

99% ^*data from raw suppliers

(5S)-5-Hydroxy-2-piperidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NCC1O
• Isomeric SMILES: C1CC(=O)NC[C@H]1O
• 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.

Technology Process of (S)-5-Hydroxypiperidin-2-one

There total 10 articles about (S)-5-Hydroxypiperidin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(S)-(+)-5-Azidomethyl-2-oxotetrahydrofuran (24211-53-8) → (S)-5-hydroxypiperidin-2-one (24211-54-9)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; In methanol; at 25 ℃; for 24h; under 760.051 Torr;

DOI:10.1080/00397911.2015.1033428

Reference yield: 85.0%

methyl 4-hydroxy-5-nitropentanoate (1179999-39-3) → (S)-5-hydroxypiperidin-2-one (24211-54-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 60 ℃; for 4h; under 2585.81 Torr; optical yield given as %ee;

DOI:10.1021/ol9018612

Reference yield:

C13H16N4O3 → (S)-5-hydroxypiperidin-2-one (24211-54-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 25 ℃; for 2h; under 760.051 Torr;

DOI:10.1080/00397911.2015.1033428

upstream raw materials:

(S)-(+)-5-Azidomethyl-2-oxotetrahydrofuran

(S)-5-tosyloxypentan-4-olide

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

(S)-(5-oxotetrahydrofuran-2-yl)methyl methanesulfonate

Downstream raw materials:

(5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one

(S)-1-benzyl-5-(benzyloxy)piperidin-2-one

(+)-1-[(5S)-5-benzyloxy-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]cyclobutanol

(+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol

Refernces

• 1、 Babu, Meruva Suresh,Raghunadh, Akula,Ramulu, Konda,Dahanukar, Vilas H.,Syam Kumar, Unniaran K.,Dubey, P. Kumar. "A practical and enantiospecific synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ols". . p. 1507 - 1515. Retrieved 2015/02/19.
• 2、 Heller, Eberhard,Lautenschl?ger, Werner,Holzgrabe, Ulrike. "Microwave-enhanced hydrogenations at medium pressure using a newly constructed reactor". . p. 1247 - 1249. Retrieved 2007/10/03.