130147-41-0

Basic information

• Product Name: 1-Pyrrolidinecarboxylicacid,2-cyano-,methylester(9CI)
• Synonyms: 1-Pyrrolidinecarboxylicacid,2-cyano-,methylester(9CI);2-cyano-1-Pyrrolidinecarboxylic acid Methyl ester
• CAS NO: 130147-41-0
• Molecular Formula: C₇H₁₀N₂O₂
• Molecular Weight: 0
• Product Categories: CARBOXYLICESTER
• Mol File: 130147-41-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Pyrrolidinecarboxylicacid,2-cyano-,methylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylicacid,2-cyano-,methylester(9CI)(130147-41-0)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylicacid,2-cyano-,methylester(9CI)(130147-41-0)

Safety Data

• Hazardous Substances Data: 130147-41-0(Hazardous Substances Data)

Upstream product

• 56475-80-0 N-(methoxycarbonyl)pyrrolidine 
• 7677-24-9 trimethylsilyl cyanide 
• 119910-06-4 2-Ethoxy-pyrrolidine-1-carboxylic acid methyl ester 
• 56475-88-8 methyl 2-methoxypyrrolidine-1-carboxylate 
• 130147-34-1 2-(tert-butyldioxy)-1-(methoxycarbonyl)pyrrolidine 

Downstream Products

• 144688-80-2 α-benzyl-N-methoxycarbonylpyrrolidine 
• 144688-71-1 α-benzyl-α-cyano-N-methoxycarbonylpyrrolidine 

Relevant articles and documents

Direct electrochemical α-cyanation of N-protected cyclic amines

α-Cyanation of N-protected cyclic amines was achieved using a direct electrochemical method. Unsubstituted N-protected cyclic amines were easily cyanated at the α-position using an undivided cell in high yields; moreover, α-cyanation of α′-substituted pyrrolidine and α′-,β′- or γ-substituted piperidines smoothly proceeded in high yield and with high to excellent diastereoselectivity. α-Substituted N-cyano-pyrrolidines and -piperidines were also cyanated at the more substituted position (the α-position) using a divided cell with high yield and high regioselectivity.

Electroorganic chemistry 139. Electroreductive decyanation of nitriles and its application to synthesis of α-alkylamines

Electroreduction of nitriles gave the corresponding decyanated products when Zn was used as the material of cathode in aprotic solvent (DMF or MeCN) containing Et4NOTs as a supporting electrolyte. Alkylation of amines at the α-position was effectively achieved by cyanation of amines at the α-position, and α-alkylation of the resultant α-amino nitriles followed by the electroreductive decyanation.

NOVEL METHOD FOR α-SUBSTITUTION OF AMINES VIA N-METHOXYCARBONYL-α-t-BUTYLDIOXYAMINES

α-Substitution of amines can be performed by ruthenium-catalyzed oxidation of N-methoxycarbonylamines with t-butyl hydroperoxide followed by treatment with nucleophiles in the presence of titanium tetrachloride.

Introduction of alkyl groups at the α-positions of pyrrolidines and piperidines: Synthesis of (±)-coniine

The conversion of lactams to α-alkylated cyclic amines is described. Reactions of α-ethoxyurethanes with trimethylsilyl cyanide in the presence of Lewis acid afford the corresponding α-cyanourethanes, which, via carbanion, are alkylated to α-alkyl-α-cyanourethanes in moderate to high yields. Syntheses of (±)-coniine and trans-quinolizidine are carried out as model experiments for dealkoxycarbonylation and decyanation of 2-alkyl-1-alkoxycarbonyl-2-cyanopiperidines.

A NEW SYNTHETIC METHOD OF α-AMINO ACIDS FROM α-METHOXYURETHANES

Reaction of α-methoxyurethanes with phenylisocyanide gave the corresponding amides of α-amino acid in reasonable yields.