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Witcha Imaram. A new synthetic route to 5-tert-butoxycarbonyl 5-methyl-1-pyrroline N-oxide. (). King Mongkut's University of Technology North Bangkok. Central Library. : , 2016.
A new synthetic route to 5-tert-butoxycarbonyl 5-methyl-1-pyrroline N-oxide
Name: Chaiyawat Aonsri
Organization :
Kasetsart University. Faculty of Science
Name: Boonsong Kongkathip
Organization :
Kasetsart University. Faculty of Science
Name: Witcha Imaram
Organization :
Kasetsart University. Faculty of Science
Email :
witcha.i@ku.ac.th
keyword:
Pyrroline
LCSH:
Organic compounds
-- Synthesis
Abstract:
EPR spin trapping is a versatile technique used to detect short-lived reactive radical
species in both chemical and biological systems. In general, a spin trapping agent, usually a
nitrone compound, is added to the system being studied to capture radicals produced in the
reaction and yield persistent nitroxide radical adducts, allowing enough time to be detected
by EPR. Recently, 5-tert-butoxycarbonyl 5-methyl-1-pyrroline N-oxide (BMPO 8), a solid
cyclic nitrone spin trap, was synthesized and exhibited several advantages over other spin
traps. For example, it can be easily purified by crystallization to remove nitroxide impurities
and more important, BMPO-superoxide radical adduct is quite stable that it does not
decompose to BMPO-hydroxyl radical adducts that could potentially lead to false
interpretation of its EPR spectrum. However, the usage of BMPO in free radical research is
quite limited due to its high cost. Thus, a more facile cost effective synthetic route to BMPO
was described in this report. The new synthetic method is based upon the availability of
starting materials in Thailand and is to improve the product yield. The key steps of the new
approach include a Michael reaction of α-nitroester 4 and ethyl acrylate 5 to dialkyl ester 6
and a subsequent selective reduction of 6 using DIBAL-H to its corresponding aldehyde 7.
The production of BMPO was achieved in 5 steps from tert-butyl alcohol 1 and 2-
bromopropionyl bromide 2. With % yield of each step given in the reaction scheme, the %
overall yield would be 22, which is higher and with a shorter synthetic route than the
previously reported BMPO synthesis
King Mongkut's University of Technology North Bangkok. Central Library
Address:
BANGKOK
Email:
library@kmutnb.ac.th
Created:
2016
Modified:
2023-01-12
Issued:
2023-01-12
บทความ/Article
application/pdf
BibliograpyCitation :
In Chemical Society of Thailand under the Patronage of Professor Dr. HRH Princess Chulabhorn and Chulalongkorn University Faculty of science. Pure and Applied Chemistry International Conference (PACCON 2016) (pp.1546-1551). Bangkok : Chemical Society of Thailand under the Patronage of Professor Dr. HRH Princess Chulabhorn
eng
©copyrights King Mongkut's University of Technology North Bangkok
RightsAccess:
ใช้เวลา
0.02729 วินาที
Chaiyawat Aonsri
| Title | Contributor | Type |
|---|---|---|
| A new synthetic route to 5-tert-butoxycarbonyl 5-methyl-1-pyrroline N-oxide
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Chaiyawat Aonsri;Boonsong Kongkathip;Witcha Imaram | บทความ/Article |
Boonsong Kongkathip
| Title | Contributor | Type |
|---|---|---|
| Effect of the binding-cavity symmetry for cholesterol in aqueous solution
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Preeyarad Charoensumran;Boonsong Kongkathip;Bunyarithi Sookcharoenpinyo | บทความ/Article | |
| A new synthetic route to 5-tert-butoxycarbonyl 5-methyl-1-pyrroline N-oxide
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Chaiyawat Aonsri;Boonsong Kongkathip;Witcha Imaram | บทความ/Article | |
| Towards the synthesis of molecular double basket
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Waramporn Boonyaporn;Boonsong Kongkathip;Bunyarithi Sookcharoenpinyo | บทความ/Article |
Witcha Imaram
| Title | Contributor | Type |
|---|---|---|
| A new synthetic route to 5-tert-butoxycarbonyl 5-methyl-1-pyrroline N-oxide
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Chaiyawat Aonsri;Boonsong Kongkathip;Witcha Imaram | บทความ/Article | |
| Study of the reaction conditions mediated synthesis of 4-thiazolidinone derivatives by one-pot three-component reaction
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Natsima Nuammee;Witcha Imaram | บทความ/Article |