25077-25-2

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Piperidinedione, 1-methylis utilized as a key intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into the molecular structures of a wide range of drugs and medicinal products. Its chemical properties, including reactivity and versatility, facilitate its use in various synthetic processes, contributing to the development of novel therapeutic agents.
Used in Drug Synthesis:
In the field of drug synthesis, 2,6-Piperidinedione, 1-methylserves as a crucial component for creating new drug molecules. Its unique structure allows for the attachment of various functional groups, enabling the design of compounds with specific therapeutic properties and improved pharmacological profiles.
Used in Medicinal Chemistry Research:
2,6-Piperidinedione, 1-methylis also employed in medicinal chemistry research to explore its potential in the development of new therapeutic agents. Researchers use 2,6-Piperidinedione, 1-methyl- to investigate its interactions with biological targets and to understand its role in modulating biological processes, which can lead to the discovery of innovative treatments for various diseases.

InChI:InChI=1/C6H9NO2/c1-7-5(8)3-2-4-6(7)9/h2-4H2,1H3

Upstream product

• 931-20-4 1-methylpiperidin-2-one 
• 1121-89-7 piperidine-2,6-dione 
• 74-88-4 methyl iodide 
• 110-94-1 1,5-pentanedioic acid 
• 74-89-5 methylamine 
• 186581-53-3 diazomethane 

Downstream Products

• 29954-00-5 5-oxo-5-phenyl-valeric acid methylamide 
• 626-67-5 N-methylcyclohexylamine 
• 931-20-4 1-methylpiperidin-2-one 
• 100609-21-0 5-Oxo-6-phenyl-hexansaeure-⁽¹⁾-methylamid 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 147767-29-1 3-(3-phenylpropyl)-1-methylglutarimide 
• 147767-28-0 3-(2-phenylethyl)-1-methylglutarimide 
• 143-07-7 lauric acid 
• 2363-71-5 heneicosanoic acid 
• 6250-70-0 1,19-nonadecanedioic acid 
• 1002-84-2 palmitic acid 
• 506-12-7 heptadecanoic acid 
• 16424-31-0 5-oxotteradecanoic acid 
• 93479-66-4 5-oxoheptadecanoic acid 

Relevant academic research and scientific papers

A METHOD FOR FLUORINATED RING-OPENING OF A SUBSTRATE

Disclosed herein, inter alia, are methods useful for making a fluoroalkyl amine and methods useful for making an α-oxygenated cyclic amine.

Catalytic enantio- and diastereoselective alkylations with cyclic sulfamidates

(Figure Presented) Open for business: The enantio- and diastereoselective nucleophilic ring opening of five-membered and six-membered cyclic sulfamidates under asymmetric phase-transfer catalysis is presented. A range of pro-nucleophiles have been successfully alkylated in good yields and in good to excellent enantioselectivites.

Unique oxidation reaction of amides with pyridine-N-oxide catalyzed by ruthenium porphyrin: Direct oxidative conversion of N-acyl-L-proline to N-acyl-L-glutamate

Oxidations of alkanes, alkenes, and aromatic rings with pyridine N-oxides are efficiently catalyzed by ruthenium porphyrins under mild conditions. We show here that the oxidation of N-acyl cyclic amines with RuIVtetraarylporphyrin dichloride-2,6-substituted pyridine N-oxides directly gives N-acyl amino acids in modest to good yield via oxidative C-N bond cleavage. N-Acylpyrrolidines and N-acylpiperidines were converted to N-acyl-γ-aminobutyric acids and N-acyl-δ-aminovaleric acids, respectively. This type of reaction is a novel one in which the C-N bond is cleaved selectively at the less substituted carbon. Notably, the proline residue in proline-containing peptides was selectively converted to glutamate. A large intramolecular kinetic isotope effect (kH/kD = 9.8) was observed in the oxidation of N-benzoyl[2,2,-d2]pyrrolidine, indicating that the reaction should involve an α-hydrogen atom abstraction process as the rate-determining step. N-Acylcarbaldehyde, the putative intermediate ring-opened form of α-hydroxylated N-acyl cyclic amine, was readily oxidized with the oxidizing system to afford the corresponding N-acylamino acid in good yield. Further, lactams (1-methyl-2-pyrrolidone and 1-methyl- 2-piperidone) were also oxidized to give the corresponding imides (1-methylsuccinimide and 1-methylpiperidine-2,6-dione). Copyright

Niobium pentachloride-mediated nucleophilic additions to cyclic N-acyliminium ions

Niobium chloride promoted the nucleophilic addition of allyltrimethylsilane, ethyl acetoacetate, indole and the silyl enol ether derived from acetone to cyclic N-acyliminium ions. The products were obtained in good yields.

Chemical and microsomal oxidation of tertiary amides: Regio- and stereoselective aspects

The conformationally restricted tertiary amides N-methyl-2-pyrrolidone 6, N-methyl-2-piperidone 7 and N-methyl-ε-caprolactam 8 were oxidised by 5,10,15,20-tetraphenylporphyrinatoiron(III) chloride/tert-butyl hydroperoxide (TPPFe/ButOOH) and by phenobarbital-induced rat liver microsomes. The products were the N-demethylated lactams together with the analogous N-methylimides and norimides. For the TPPFe/ButOOH reaction ring oxidation is preferred to N-demethylation, paralleling the relative stabilities of the corresponding intermediate carbon-centred radicals as calculated by the AM1 semi-empirical method. In contrast, the microsomal reaction of the N-methyllactams strongly favours N-demethylation, demonstrating that hydrogen atom abstraction from the alkyl group Z to the amide carbonyl oxygen atom is preferred. The chiral tertiary amides N-methyl-N-(1-phenylethyl)benzamide 9 and N-methyl-5-phenyl-2-pyrrolidone 10 were also oxidised by TPPFe/ButOOH and by phenobarbital-induced rat liver microsomes. Using TPPFe/ButOOH, loss of the secondary alkyl group of 9 is preferred by a factor of ca. 6. Similarly, ring oxidation of 10 is favoured over demethylation by a factor of 9. For the microsomal reaction of (R)-9 dealkylation is preferred over demethylation by a factor of 1.7, whereas for (S)-9 demethylation is favoured by a factor of 1.25. For the microsomal reaction of (R)-10 and (S)-10 ring oxidation at the 5-position of the pyrrolidone ring is preferred over demethylation by factors of ca. 4 and 9 for the two isomers, respectively, and the (S)-enantiomer undergoes ring oxidation 2-3 times more readily than the (R)-enantiomer. For both 9 and 10 there is negligible stereochemical influence of the chiral centre upon the N-demethylation reaction. The results show that the stereochemical preference of the microsomal N-dealkylation reaction is modest.

Stereocontrolled formation of epoxy peroxide functionality appended to a lactam ring

The action of tert-butyl hydroperoxide and tin(IV) chloride upon allylic alcohols containing a lactam ring leads mainly to epoxy alkyl peroxides with high diastereoselection. Both the stereochemistry and the products formed are in marked contrast to the r

Tin(IV)-mediated stereoselective synthesis of epoxides with concomitant alkyl peroxide formation

Epoxy alkyl peroxides are formed stereoselectively by the action of t-butyl hydroperoxide-SnCl4 upon allylic alcohols containing an amido group, and with reversal of the diastereoselectivity shown by the action of t-butyl hydroperoxide-VO(acac)2 upon analogous carbocyclic alcohols.

A FACILE SYNTHESIS OF dl-SEDAMINE AND dl-ALLOSEDAMINE

Racemic sedamine and dl-allosedamine were easily synthesized from the intermediate (3) using a cyclic acyliminium salt by the addition-elimination reaction sequence.

Ruthenium Tetroxide Oxidation of N-Alkyllactams

Ruthenium tetroxide (RuO4) oxidation of N-alkyllactams proceeded regioselectively depending on the size of lactam ring, except for the seven-membered ring.Four- and eight-membered N-methyl- and N-ethyllactams were oxidized at the exocyclic α-carbon adjacent to nitrogen to produce the N-acyllactams and NH-lactams, while five- and six-membered lactams underwent endocyclic oxidation to yield the cyclic imides.Oxidation of seven-membered lactams yielded a mixture of products arising from both exocyclic and endocyclic oxidations.These regioselectivities were confirmed in the oxidation of substrates having a tertiary carbon at the oxidation position.Keywords---oxidation; ruthenium tetroxide oxidation; regioselective oxidation; hydroxylation; imide synthesis; N-alkyllactam; N-acyllactams; imide; ruthenium tetroxide; two-phase method