51856-76-9Relevant academic research and scientific papers
Novel process for preparing 1-methyl-2-(2-hydroxyethyl)pyrrolidine
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, (2020/03/05)
The present invention relates to a method for synthesizing 1-methyl-2-(2-hydroxyethyl)pyrrolidine, which is useful as an intermediate of a pharmaceutical. More specifically, the present invention relates to a novel synthesis method which uses metal borohydride as a reducing agent in a process of manufacturing 1-methyl-2-(2-hydroxyethyl)pyrrolidine, which is a target substance, from methyl (2E/Z)-2-(1-methylpyrrolidinyridin-2-ylidene)acetate, wherein the methyl (2E/Z)-2-(1-methylpyrrolidinyridin-2-ylidene)acetate is reduced in two stages sequentially, thereby being able to obtain the target substance with a safe process and cheap cost compared to an existing method.COPYRIGHT KIPO 2020
An efficient process of preparation of 1-methyl-2-(2-hydroxyethyl)pyrrolidine for production in ton scale
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, (2017/04/25)
The present invention relates to a safe, simple and novel manufacturing method of 1-methyl-2-(2-hydroxyethyl)pyrrolidine as a drug medium, capable of mass production. 1-methyl-2-(2-hydroxyethyl)pyrrolidine can be manufactured by: reducing a double bond into a single bond through hydrogenation reaction in the presence of palladium on carbon (Pd on C) catalyst, and sequentially reducing an ester group into an alcohol group with a reducing agent such as NaBH_4 or LiBH_4; reducing a double bond and an ester group at a single reaction at the same time; or performing enantioselective hydrogenation of allylic alcohol with a chiral catalyst.
Radical cyclization reactions of α-silyl amine α,β-unsaturated ketone and ester systems promoted by single electron transfer photosensitization
Jeon, Yoon T.,Lee, Chao-Pin,Mariano, Patrick S.
, p. 8847 - 8863 (2007/10/02)
The results of a broad investigation of the preparative and mechanistic aspects of single electron transfer (SET) promoted photocyclization reactions of α-silyl amino and amido α,β-unsaturated esters and ketones are presented. A number of unique and synthetically useful features of these processes, driven by α-silyl amine and amide cation radical desilylation and by intramolecular conjugate addition of intermediate α-amino and α-amido carbon-centered radicals to unsaturated esters and ketones, are described. Comparisons of the SET-sensitized and direct irradiation promoted reactions of these systems have shown how the former method is superior in inducing photocyclization reactions in cases where the α,β-unsaturated ketone or ester excited states are too reactive to be quenched by SET from the tethered amine donors and where diradicals produced as intermediates in the direct-irradiation reactions undergo fragmentation rather than cyclization. The current efforts have also demonstrated that problems associated with the ready oxidation of intermediate α-amino radicals can be avoided by the proper selection of photosensitizer or amine N substituents. Lastly, the synthetic versatility of this chemistry, exemplified by its application to the preparation of a number of N-heterocyclic substances by pathways involving either exo or endo radical cyclization, is presented.
1-METHYLPYRROLIDINE-2-ACETIC ACID, A PLAUSIBLE INTERMEDIATE IN THE BIOSYNTHESIS OF COCAINE
Leete, Edward
, p. 481 - 487 (2007/10/02)
Radioactive 1-methylpyrrolidine-2-acetic acid (0.5percent absolute incorporation) was isolated from Erythroxylum coca plants which had been fed 14C>-1-methyl-Δ1-pyrrolinium chloride.A systematic degradation of the 1-methylpyrrolidine-2-acetic acid established that all the radioactivity was located at its C-2 position.Since the cocaine isolated from this feeding experiment was labeled at C-5, this result is consistent with the hypothesis that 1-methylpyrrolidine-2-acetic acid, or a suitably activated ester, is an intermediate in the biosynthesis of cocaine.
