(+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID

Base Information

• Chemical Name: (+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID
• CAS No.: 123811-83-6
• Molecular Formula: C12H21NO4
• Molecular Weight: 243.303
• Mol file: 123811-83-6.mol

Synonyms:(+/-)-CIS-N-BOC-4-METHYL-PIPECOLINIC ACID;(+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID

Chemical Property of (+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID

Chemical Property:

• PSA: 66.84000
• LogP: 2.04450

Purity/Quality:

98%min ^*data from raw suppliers

(+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID

There total 7 articles about (+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC 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: 89.0%

carbon dioxide (124-38-9,18923-20-1) + 4-methylpiperidine-1-carboxylic acid tert-butyl ester (123387-50-8) → (+/-)-cis-Boc-4-methylpipecolinic acid (123811-83-6,661459-03-6,182509-19-9)

Guidance literature:

4-methylpiperidine-1-carboxylic acid tert-butyl ester; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; cyclohexane; at -78 - 20 ℃; for 1h;

carbon dioxide; In diethyl ether; cyclohexane; at -78 ℃; for 0.25h;

Reference yield: 66.0%

di-tert-butyl dicarbonate (24424-99-5) + (+/-)-cis-4-methylpipecolic acid (69081-79-4,69081-80-7,74874-06-9,74892-81-2,79199-63-6) → (+/-)-cis-Boc-4-methylpipecolinic acid (123811-83-6,661459-03-6,182509-19-9)

Guidance literature:

With sodium hydroxide; In tert-butyl alcohol; for 24h; Ambient temperature; pH at 9.5;

DOI:10.1021/jo00289a058

Reference yield:

4-methylpyridine-1-oxide (1003-67-4) → (+/-)-cis-Boc-4-methylpipecolinic acid (123811-83-6,661459-03-6,182509-19-9)

Guidance literature:

Multi-step reaction with 4 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

4: 66 percent / 2 N NaOH / 2-methyl-propan-2-ol / 24 h / Ambient temperature; pH at 9.5

With hydrogenchloride; sodium hydroxide; hydrogen; N,N-Dimethylcarbamoyl chloride; platinum(IV) oxide; In ethanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo00289a058

upstream raw materials:

di-tert-butyl dicarbonate

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

carbon dioxide

4-methylpiperidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

C₁₂H₂₁NO₄

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

Refernces

• 1、 Cossy, Janine,Belotti, Damien. "Direct diastereoselective synthesis of (±)-cis- and (±)-trans-4-methylpipecolic acid and derivatives". . p. 2119 - 2120. Retrieved 2007/10/03.