(2R-cis)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester

Base Information

• Chemical Name: (2R-cis)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester
• CAS No.: 79199-61-4
• Molecular Formula: C₉H₁₇NO₂
• Molecular Weight: 171.239
• Mol file: 79199-61-4.mol

Synonyms:(2R,4S)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester;(2R-cis)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester;Ethyl (2R,4S)-4-Methylpipecolate;Argatroban Impurity 2

Chemical Property of (2R-cis)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester

Chemical Property:

• Boiling Point: 226.1±33.0 °C(Predicted)
• PKA: 6.65±0.10(Predicted)
• PSA: 38.33000
• Density: 0.969±0.06 g/cm3(Predicted)
• LogP: 1.26640

Purity/Quality:

> 95% ^*data from raw suppliers

Ethyl(2R,4S)-4-Methylpipecolate,90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Ethyl (2R,4S)-4-Methylpipecolate is an intermediate in the preparation of Argatroban (A769000).

Technology Process of (2R-cis)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester

There total 7 articles about (2R-cis)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester 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: 97.6%

ethyl (2R,4S)-4-methyl-2-piperidinecarboxylate L-(-)-dibenzoyl tartrate → ethyl 4-methylpipeloate (79199-61-4,42205-75-4)

Guidance literature:

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

Reference yield: 35.6%

ethyl (2R,4S)-4-methyl-2-piperidinecarboxylate L-(+)-tartarate → ethyl 4-methylpipeloate (79199-61-4,42205-75-4)

Guidance literature:

ethyl (2R,4S)-4-methyl-2-piperidinecarboxylate L-(+)-tartarate; With 1-butylpyridinium bromide; In water; isopropyl alcohol; at 65 ℃;

With potassium carbonate; at 48 ℃;

Reference yield:

(2R,4S)-ethyl 4-methyl-1-((S)-1-phenylethyl)piperidine-2-carboxylate (1350815-39-2) → ethyl 4-methylpipeloate (79199-61-4,42205-75-4)

Guidance literature:

With 10% palladium hydroxide on charcoal; hydrogen; In ethanol; at 20 ℃; for 4h; under 760.051 Torr;

DOI:10.1016/j.tetasy.2011.09.009

upstream raw materials:

(2R,4S)-4-Methyl-1-((R)-1-phenyl-ethyl)-piperidine-2-carboxylic acid ethyl ester

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

isoprene

(2R,4S)-ethyl 4-methyl-1-((S)-1-phenylethyl)piperidine-2-carboxylate

Refernces

• 1、 Ferraboschi, Patrizia,Mieri, Maria De,Grisenti, Paride,Lotz, Matthias,Nettekoven, Ulrike. "Diastereoselective synthesis of an argatroban intermediate, ethyl (2R,4R)-4-methylpipecolate, by means of a Mandyphos/rhodium complex-catalyzed hydrogenation". experimental part. p. 1626 - 1631. Retrieved 2012/01/03.