(2S-trans)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester

Base Information

• Chemical Name: (2S-trans)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester
• CAS No.: 78306-52-2
• Molecular Formula: C9H17NO2
• Molecular Weight: 171.239
• Mol file: 78306-52-2.mol

Synonyms:(2S,4S)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester;(2S-trans)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester;Ethyl (2S,4S)-4-Methylpipecolate;Argatroban Related CoMpound (Ethyl (2S,4S)-4-Methylpipecolate)

Chemical Property of (2S-trans)-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:

95-99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2S-trans)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester

There total 6 articles about (2S-trans)-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: 97.7%

(2S,4S)-4-methyl-2-piperidine carboxylic acid ethyl ester D-tartaric acid salt → ethyl (2S,4S)-4-methylpiperidine-2-carboxylate (78306-52-2,42205-75-4)

Guidance literature:

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

Reference yield: 51.0%

ethyl trans-(2S,4R)-1-<(R)-1-phenylethyl>-4-methylpipecolate (134984-77-3) → ethyl (2S,4S)-4-methylpiperidine-2-carboxylate (78306-52-2,42205-75-4)

Guidance literature:

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

Reference yield:

ethyl 4-methyl-2-piperidinecarboxylate L-tartrate → ethyl (2R-trans)-4-methylpiperidine-2-carboxylate (74892-82-3,42205-75-4) + ethyl (2S,4S)-4-methylpiperidine-2-carboxylate (78306-52-2,42205-75-4)

Guidance literature:

With potassium carbonate; In water; ethyl acetate; at 15 - 20 ℃; for 1.08333h; Overall yield = 85 %; Overall yield = 29.4 g;

upstream raw materials:

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

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

isoprene

(2S,4S)-4-methyl pipecolic acid

Refernces

• 1、 -. "PROCESS INTERMEDIATES AND METHODS FOR THE PREPARATION OF PROCESS INTERMEDIATES FOR THE SYNTHESIS OF ARGATROBAN MONOHYDRATE". Paragraph 0089. . Retrieved 2014/04/03.
• 2、 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.