Ethyl 3-methoxy-4-oxopiperidine-1-carboxylate

Base Information

• Chemical Name: Ethyl 3-methoxy-4-oxopiperidine-1-carboxylate
• CAS No.: 83863-72-3
• Molecular Formula: C₉H₁₅NO₄
• Molecular Weight: 201.222
• Hs Code.: 2933399090
• European Community (EC) Number: 281-138-0
• DSSTox Substance ID: DTXSID801003986
• Nikkaji Number: J326.947G
• Mol file: 83863-72-3.mol

Synonyms:83863-72-3;Ethyl 3-methoxy-4-oxopiperidine-1-carboxylate;N-Carbethoxy-3-methoxy-4-piperidone;EINECS 281-138-0;156970-96-6;3-methoxy-4-oxo-piperidine-1-carboxylic acid ethyl ester;1-Piperidinecarboxylic acid, 3-methoxy-4-oxo-, ethyl ester, (-)-;1-PIPERIDINECARBOXYLIC ACID, 3-METHOXY-4-OXO-, ETHYL ESTER;1-carbethoxy-3-methoxy-4-piperidone;SCHEMBL715562;3-Methoxy-4-oxo-1-piperidinecarboxylic acid ethyl ester;WDPDIPXYVCLBCI-UHFFFAOYSA-N;DTXSID801003986;MFCD02093811;AKOS015919204;AB10847;AC-6362;AS-37197;CS-0134062;Ethyl3-methoxy-4-oxopiperidine-1-carboxylate;FT-0762149;ethyl 3-methoxy-4-oxo-1-piperidinecarboxylate

Chemical Property of Ethyl 3-methoxy-4-oxopiperidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 0.00106mmHg at 25°C
• Refractive Index: 1.481
• Boiling Point: 301.3 °C at 760 mmHg
• Flash Point: 136 °C
• PSA: 55.84000
• Density: 1.16 g/cm³
• LogP: 0.37060
• Storage Temp.: 2-8°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 201.10010796
• Heavy Atom Count: 14
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

N-Carbethoxy-3-methoxy-4-piperidone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1CCC(=O)C(C1)OC

Technology Process of Ethyl 3-methoxy-4-oxopiperidine-1-carboxylate

There total 4 articles about Ethyl 3-methoxy-4-oxopiperidine-1-carboxylate 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: 99.0%

(-)-ethyl 3,4,4-trimethoxy-1-piperidinecarboxylate (83863-73-4,156970-95-5) → (-)-ethyl 3-methoxy-4-oxo-1-piperidine-carboxylate (83863-72-3,156970-96-6)

Guidance literature:

With hydrogenchloride; methanol; In 1,4-dioxane; at 20 ℃; for 4h;

Reference yield:

N-ethoxycarbonyl-4-piperidone (29976-53-2) → (-)-ethyl 3-methoxy-4-oxo-1-piperidine-carboxylate (83863-72-3,156970-96-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) H⁺ / 2.) heating

2: 1.) lead tetraacetate, BF₃*Et₂O, 2.) H₂SO₄ / 1.) room temperature, 2 h, 2.) H₂O, 1 h.

With lead(IV) acetate; sulfuric acid; boron trifluoride diethyl etherate; hydrogen cation;

DOI:10.1080/00397919808005072

Reference yield:

ethyl 3-hydroxy-4,4-dimethoxy-1-piperidinecarboxylate (83898-43-5) → (-)-ethyl 3-methoxy-4-oxo-1-piperidine-carboxylate (83863-72-3,156970-96-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

1.2: 20 °C

2.1: sulfuric acid / water; tetrahydrofuran / 2 h / 60 °C

With sulfuric acid; sodium hydride; In tetrahydrofuran; water;

DOI:10.1021/jm500462x

upstream raw materials:

methanol

4-Methoxy-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester

N-ethoxycarbonyl-4-piperidone

(-)-ethyl 3,4,4-trimethoxy-1-piperidinecarboxylate

Downstream raw materials:

ethyl (-)-cis-4-amino-3-methoxy-1-piperidinecarboxylate

cis(+/-) ethyl 4-amino-3-methoxypiperidine-1-carboxylate

Refernces

• 1、 Park, Jung Sang,Im, Weonbin,Choi, Sunghak,Park, Sook Jin,Jung, Jun Min,Baek, Ki Seon,Son, Han Pyo,Sharma, Satyasheel,Kim, In Su,Jung, Young Hoon. "Discovery and SAR of N-(1-((substituted piperidin-4-yl)methyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamide derivatives: 5-Hydroxytryptamine receptor 4 agonist as a potent prokinetic agent". . p. 75 - 88. Retrieved 2016/01/09.
• 2、 -. "3-Aminocyclopentanecarboxamides as Modulators of Chemokine Receptors". Page/Page column 27. . Retrieved 2010/11/27.