(S)-3-hydroxypiperidin-2-one

Base Information

• Chemical Name: (S)-3-hydroxypiperidin-2-one
• CAS No.: 74954-71-5
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.132
• Hs Code.: 2933790090
• DSSTox Substance ID: DTXSID10415363
• Nikkaji Number: J1.047.004H
• Wikidata: Q27467528
• Mol file: 74954-71-5.mol

Synonyms:(S)-3-hydroxypiperidin-2-one;74954-71-5;(3S)-3-HYDROXYPIPERIDIN-2-ONE;3-(S)-HYDROXY-2-PIPERIDONE;XYLOSE-DERIVED ISOFAGOMINE LACTAM;(3S)-3-Hydroxy-2-piperidinone;3beta-Hydroxypiperidine-2-one;SCHEMBL1105058;DTXSID10415363;RYKLZUPYJFFNRR-BYPYZUCNSA-N;(S)-(-)-3-hydroxy-2-piperidone;AKOS016844259;AT24626;CS-0455353;A850531;Q27467528

Chemical Property of (S)-3-hydroxypiperidin-2-one

Chemical Property:

• Melting Point: 144-146℃ (ethyl acetate )
• PSA: 49.33000
• LogP: -0.41390
• Storage Temp.: 2-8°C
• XLogP3: -0.6
• 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:

97% ^*data from raw suppliers

(S)-3-Hydroxypiperidin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(=O)NC1)O
• Isomeric SMILES: C1C[C@@H](C(=O)NC1)O
• Uses: (S)-3-Hydroxypiperidin-2-one is used in synthesis of alkaloid (S)-3-Hydroxypiperidin-2-one and its O-TBS protected derivatives.

Technology Process of (S)-3-hydroxypiperidin-2-one

There total 9 articles about (S)-3-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: 78.0%

(S)-3-(tert-butyldimethylsilyloxy)piperidine-2-one (937740-20-0) → (S)-3-hydroxypiperidin-2-one (74954-71-5,220928-01-8)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 6h;

DOI:10.1002/jhet.5570440239

Reference yield:

6-nitro-3-oxo-2-(triphenyl-λ5-phosphanylidene)-hexanenitrile → (S)-3-hydroxypiperidin-2-one (74954-71-5,220928-01-8)

Guidance literature:

Multi-step reaction with 5 steps

1: ozone / CH₂Cl₂

2: lipase from Candida rugosa

3: BS-LDH, FDH, NADH

5: hydrogen / platinum(IV) oxide

With 1,4-dihydronicotinamide adenine dinucleotide; lipase from Candida rugosa; hydrogen; ozone; platinum(IV) oxide; In dichloromethane;

DOI:10.1016/S0040-4039(99)80114-2

Reference yield:

(S)-2-hydroxy-5-nitropentanoic acid methyl ester (220927-99-1) → (S)-3-hydroxypiperidin-2-one (74954-71-5,220928-01-8)

Guidance literature:

With hydrogen; platinum(IV) oxide; Yield given;

DOI:10.1016/S0040-4039(99)80114-2

upstream raw materials:

(S)-2-hydroxy-5-nitropentanoic acid methyl ester

(S)-3-(tert-butyldimethylsilyloxy)piperidine-2-one

methyl 5-nitro-2-oxopentanoate

5-nitro-2-oxopentanoic acid

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