(+/-)-cis-4-methylpipecolic acid

Base Information

• Chemical Name: (+/-)-cis-4-methylpipecolic acid
• CAS No.: 79199-63-6
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.186
• Mol file: 79199-63-6.mol

Synonyms:

Chemical Property of (+/-)-cis-4-methylpipecolic acid

Chemical Property:

Purity/Quality:

(2S,4S)-4-Methyl-pipecolinicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+/-)-cis-4-methylpipecolic acid

There total 4 articles about (+/-)-cis-4-methylpipecolic acid 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: 100.0%

(+/-)-cis-Boc-4-methylpipecolinic acid (123811-83-6,661459-03-6,182509-19-9) → (+/-)-cis-4-methylpipecolic acid (69081-79-4,69081-80-7,74874-06-9,74892-81-2,79199-63-6)

Guidance literature:

With hydrogenchloride; In ethyl acetate;

DOI:10.1016/S0040-4039(01)00138-1

Reference yield: 92.0%

4-Methyl-pyridine-2-carboxylic acid; hydrochloride (123811-73-4) → (+/-)-cis-4-methylpipecolic acid (69081-79-4,69081-80-7,74874-06-9,74892-81-2,79199-63-6)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; water; at 60 ℃; for 24h; under 3102.9 Torr;

DOI:10.1021/jo00289a058

Reference yield:

4-methylpyridine-1-oxide (1003-67-4) → (+/-)-cis-4-methylpipecolic acid (69081-79-4,69081-80-7,74874-06-9,74892-81-2,79199-63-6)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethylcarbamyl chloride / CH₂Cl₂ / 24 h / Ambient temperature

2: 93 percent / 6 N HCl / 24 h / Heating

3: 92 percent / hydrogen / platinum oxide / ethanol; H₂O / 24 h / 60 °C / 3102.9 Torr

With hydrogenchloride; hydrogen; N,N-Dimethylcarbamoyl chloride; platinum(IV) oxide; In ethanol; dichloromethane; water;

DOI:10.1021/jo00289a058

upstream raw materials:

4-Methyl-pyridine-2-carboxylic acid; hydrochloride

(+/-)-cis-Boc-4-methylpipecolinic acid

4-methylpyridine-1-oxide

2-Cyano-4-methylpyridin

Downstream raw materials:

(+/-)-cis-Boc-4-methylpipecolinic acid

ethyl (2S,4S)-4-methylpiperidine-2-carboxylate

Refernces

• 1、 Shuman, Robert T.,Ornstein, Paul L.,Paschal, Jonathan W.,Gesellchen, Paul D.. "An Improved Synthesis of Homoproline and Derivatives". . p. 738 - 741. Retrieved 2007/10/02.