(2S,4R)-Ethyl 4-methylpiperidine-2-carboxylate

Base Information

• Chemical Name: (2S,4R)-Ethyl 4-methylpiperidine-2-carboxylate
• CAS No.: 79199-62-5
• Molecular Formula: C₉H₁₇NO₂
• Molecular Weight: 171.239
• DSSTox Substance ID: DTXSID901179419
• Mol file: 79199-62-5.mol

Synonyms:79199-62-5;(2S,4R)-Ethyl 4-methylpiperidine-2-carboxylate;ethyl (2S,4R)-4-methylpiperidine-2-carboxylate;(2S-cis)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester;Ethyl (2S,4R)-4-Methylpipecolate;starbld0017180;DTXSID901179419;CS-0163976;F78215;EN300-23006207;rac-ethyl (2R,4S)-4-methylpiperidine-2-carboxylate;2-Piperidinecarboxylic acid, 4-methyl-, ethyl ester, (2S-cis)-;(2S-cis)-4-Methyl-2-piperidineCarboxylic Acid Ethyl Ester (Afatinib Impurity pound(c)

Chemical Property of (2S,4R)-Ethyl 4-methylpiperidine-2-carboxylate

Chemical Property:

• PSA: 38.33000
• LogP: 1.26640
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 171.125928785
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

> 95% ^*data from raw suppliers

Ethyl(2S,4R)-4-Methylpipecolate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1CC(CCN1)C
• Isomeric SMILES: CCOC(=O)[C@@H]1C[C@@H](CCN1)C
• Uses: Ethyl (2S,4R)-4-Methylpipecolate is an intermediate in the preparation of Argatroban (A769000).

Technology Process of (2S,4R)-Ethyl 4-methylpiperidine-2-carboxylate

There total 8 articles about (2S,4R)-Ethyl 4-methylpiperidine-2-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: 98.2%

(2S,4R)-4-methyl-2-piperidinecarboxylic acid ethyl ester dibenzoyl tartaric acid salt → ethyl (2S,4R)-4-methylpipecolate (79199-62-5,42205-75-4)

Guidance literature:

With sodium carbonate; In methanol; at 50 ℃; for 1h; pH=8; Temperature; pH-value; Solvent;

Reference yield: 72.0%

ethyl cis-(2S,4R)-1-<(R)-1-phenylethyl>-4-methylpipecolate (134984-62-6) → ethyl (2S,4R)-4-methylpipecolate (79199-62-5,42205-75-4)

Guidance literature:

With hydrogen; palladium hydroxide - carbon; In ethanol; under 760 Torr; Ambient temperature;

Reference yield: 34.6%

C4H6O6*C9H17NO2 → ethyl (2S,4R)-4-methylpipecolate (79199-62-5,42205-75-4)

Guidance literature:

With sodium carbonate; In methanol; at 48 ℃;

upstream raw materials:

ethyl cis-(2S,4R)-1-<(R)-1-phenylethyl>-4-methylpipecolate

(6S)-1-<(R)-1-phenylethyl>-6-ethoxycarbonyl-4-methyl-3,4-didehydropiperidine

isoprene

4(R)-Methylpiperidine-2(R)-carboxylic acid ethyl ester

Refernces

• 1、 Bailey, Patrick D.,Wilson, Robert D.,Brown, George R.. "Enantio- and Diastereo-selective Synthesis of Pipecolic Acid Derivatives using the Aza-Diels-Alder Reaction of Imines with Dienes". . p. 1337 - 1340. Retrieved 2007/10/02.