3-Methoxycarbonyl-2,2,5,5-tetramethyl-3-pyrrolidin-1-oxyl

Base Information

• Chemical Name: 3-Methoxycarbonyl-2,2,5,5-tetramethyl-3-pyrrolidin-1-oxyl
• CAS No.: 2154-32-7
• Molecular Formula: C10H16 N O3
• Molecular Weight: 198.242
• Mol file: 2154-32-7.mol

Synonyms:3-Pyrrolin-1-yloxy,3-carboxy-2,2,5,5-tetramethyl-, methyl ester (7CI,8CI); 2,2,5,5-Tetramethyl-4-methoxycarbonylpyrroline-1-oxyl;3-Methoxycarbonyl-2,2,5,5-tetramethylpyrroline-1-oxyl; CMPO

Chemical Property of 3-Methoxycarbonyl-2,2,5,5-tetramethyl-3-pyrrolidin-1-oxyl

Chemical Property:

• Melting Point: 74-76°C
• PSA: 29.54000
• LogP: 1.32190
• Storage Temp.: -20°C Freezer

Purity/Quality:

97% ^*data from raw suppliers

3-Methoxycarbonyl-2,2,5,5-tetramethyl-3-pyrrolidin-1-oxyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A spin label A spin label.

Technology Process of 3-Methoxycarbonyl-2,2,5,5-tetramethyl-3-pyrrolidin-1-oxyl

There total 6 articles about 3-Methoxycarbonyl-2,2,5,5-tetramethyl-3-pyrrolidin-1-oxyl 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%

2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-carboxylic acid methyl ester (70473-81-3) → methyl 1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-carboxylate radical (2154-32-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In diethyl ether; at 0 - 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/jacs.6b05421

Reference yield:

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → methyl 1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-carboxylate radical (2154-32-7)

Guidance literature:

Multi-step reaction with 3 steps

1: bromine / acetic acid / 24 h / 20 °C

2: sodium methylate / methanol / 20 °C

3: dihydrogen peroxide; sodium tungstate; sodium hydrogencarbonate / methanol; water / 72 h

With sodium tungstate; dihydrogen peroxide; bromine; sodium methylate; sodium hydrogencarbonate; In methanol; water; acetic acid;

DOI:10.1016/j.saa.2016.06.021

Reference yield:

3,5-Dibromo-4-oxo-2,2,6,6-tetramethylpiperidine Hydrobromide (19971-12-1) → methyl 1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-carboxylate radical (2154-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methylate / 3 h / 0 - 20 °C / Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / diethyl ether / 1.5 h / 0 - 20 °C / Inert atmosphere

With sodium methylate; 3-chloro-benzenecarboperoxoic acid; In diethyl ether;

DOI:10.1021/jacs.6b05421

upstream raw materials:

diazomethane

3-carboxy-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy

2,2,6,6-Tetramethyl-4-piperidone

3,5-dibromo-2,2,6,6-tetramethylpiperidin-4-one

Downstream raw materials:

(1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)methyl methanesulfonate

3-(bromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-oxyl

(2,5-dihydro-2,2,5,5-tetramethyl-1-oxyl-1H-pyrrol-3-yl)methanol

trans-3-methoxycarbonyl-2,2,5,5-tetramethyl-4-phenylpyrrolidin-1-oxyl

Refernces

• 1、 Vuong, Wayne,Mosquera-Guagua, Fabricio,Sanichar, Randy,McDonald, Tyler R.,Ernst, Oliver P.,Wang, Lei,Vederas, John C.. "Synthesis of Chiral Spin-Labeled Amino Acids". . p. 10149 - 10153. Retrieved 2019/12/24.
• 2、 Haugland, Marius M.,El-Sagheer, Afaf H.,Porter, Rachel J.,Pe?a, Javier,Brown, Tom,Anderson, Edward A.,Lovett, Janet E.. "2′-Alkynylnucleotides: A Sequence- and Spin Label-Flexible Strategy for EPR Spectroscopy in DNA". . p. 9069 - 9072. Retrieved 2016/08/05.