(R)-6-(Hydroxymethyl)piperidin-2-one

Base Information

• Chemical Name: (R)-6-(Hydroxymethyl)piperidin-2-one
• CAS No.: 213532-95-7
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.159
• European Community (EC) Number: 836-815-0
• DSSTox Substance ID: DTXSID70447100
• Nikkaji Number: J934.646E
• Wikidata: Q72485556
• Mol file: 213532-95-7.mol

Synonyms:(R)-6-(Hydroxymethyl)piperidin-2-one;213532-95-7;(6R)-6-(hydroxymethyl)piperidin-2-one;(6R)-6-(Hydroxymethyl)-2-piperidinone;(R)-6-hydroxymethyl-piperidin-2-one;SCHEMBL4381020;DTXSID70447100;VMOQVTPKGUXWKA-RXMQYKEDSA-N;AMY16345;(R)-6-hydroxymethylpiperidin-2-one;MFCD13181561;AS-50982;CS-0214865;EN300-199840;P11606;A904131

Chemical Property of (R)-6-(Hydroxymethyl)piperidin-2-one

Chemical Property:

• Boiling Point: 346℃
• Flash Point: 163℃
• PSA: 49.33000
• Density: 1.098
• LogP: -0.02380
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

97% ^*data from raw suppliers

(6R)-6-(hydroxymethyl)piperidin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC(=O)C1)CO
• Isomeric SMILES: C1C[C@@H](NC(=O)C1)CO

Technology Process of (R)-6-(Hydroxymethyl)piperidin-2-one

There total 8 articles about (R)-6-(Hydroxymethyl)piperidin-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: 89.0%

(6R)-6-[(tert-butyldiphenylsilyl)oxymethyl]piperidin-2-one (209257-74-9) → (R)-6-hydroxymethyl-piperidin-2-one (213532-95-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; 1.) 0 deg C to r.t., 2.) r.t., 18 h;

DOI:10.1055/s-1998-2123

Reference yield:

methyl (R)-6-oxopiperidine-2-carboxylate (183890-34-8) → (R)-6-hydroxymethyl-piperidin-2-one (213532-95-7)

Guidance literature:

With sodium tetrahydroborate;

DOI:10.1016/j.bmcl.2005.03.059

Reference yield:

(4-methoxyphenyl)methyl hex-5-enoate (187851-95-2) → (R)-6-hydroxymethyl-piperidin-2-one (213532-95-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 56 percent / 1,4-bis(dihydroquininyl)anthraquinone, K₃Fe(CN)6, K₂CO₃, NaHCO₃, potassium osmate(VI) dihydrate, H₂O / 2-methyl-propan-2-ol / 12 h / 0 °C

2: 91 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: 82 percent / NaN₃ / dimethylformamide / 18 h / 80 °C

5: 84 percent / H₂ / Pd/C / ethanol / 18 h / 760 Torr / Ambient temperature

6: 89 percent / TBAF / tetrahydrofuran / 1.) 0 deg C to r.t., 2.) r.t., 18 h

With 1H-imidazole; potassium osmate(VI); sodium azide; 1,4-bis(dihydroquinidinyl)anthraquinone; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; potassium hexacyanoferrate(III); palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1055/s-1998-2123

upstream raw materials:

(6R)-6-[(tert-butyldiphenylsilyl)oxymethyl]piperidin-2-one

methyl (R)-6-oxopiperidine-2-carboxylate

D-2-aminoadipic acid

(R)-6-oxo-piperidine-2-carboxylic acid