83487-05-2

Basic information

• Product Name: 1H-Pyrrole-1,2-dicarboxylic acid, 2,3-dihydro-, dimethyl ester, (S)-
• CAS NO: 83487-05-2
• Molecular Formula: C8H11NO4
• Molecular Weight: 185.18
• Mol File: 83487-05-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole-1,2-dicarboxylic acid, 2,3-dihydro-, dimethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-1,2-dicarboxylic acid, 2,3-dihydro-, dimethyl ester, (S)-(83487-05-2)
• EPA Substance Registry System: 1H-Pyrrole-1,2-dicarboxylic acid, 2,3-dihydro-, dimethyl ester, (S)-(83487-05-2)

Safety Data

• Hazardous Substances Data: 83487-05-2(Hazardous Substances Data)

Upstream product

• 88817-72-5 (S)-5-Methoxy-2,5-bis-methoxycarbonylamino-pentanoic acid methyl ester 
• 158554-84-8 dimethyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate 
• 93271-96-6 (2S,5RS)-1,2-dimethyl-5-hydroxypyrrolidine-1,2-dicarboxylate 
• 185385-13-1 1-carbomethoxy-5-methoxy-L-proline methyl ester 
• 73689-73-3 Pyrrolidine-1,2-dicarboxylic acid dimethyl ester 

Downstream Products

• 83541-81-5 (S)-dimethyl pyrrolidine-1,2-dicarboxylate 

Relevant articles and documents

Efficient and Expeditious Protocols for the Synthesis of Racemic and Enantiomerically Pure Endocyclic Enecarbamates from N-Acyl Lactams and N-Acyl Pyrrolidines

A mild, practical, and straightforward protocol for the construction of endocyclic enecarbamates starting from N-acyl lactams and N-acyl pyrrolidines is presented. Lactams were reduced to the corresponding α-hydroxycarbamates in good to excellent yields using DIBAL-H, SuperHydride, or NaBH4 followed by β-elimination (dehydration) promoted by trifluoroacetic anhydride in the presence of hindered nitrogenated bases such as 2,6-lutidine, diisopropylethylamine, or triethylamine. Small variations of this protocol permitted the preparation of several endocyclic enecarbamates (12 examples) in good to excellent overall yields (56-96%). The protocol was demonstrated to be applicable to several ring sizes, compatible with different protecting groups, and to be mild enough to prevent racemization of racemization-prone stereocenters. The efficacy of the procedure in the preparation of enantiomerically pure endocyclic enecarbamates was also demonstrated and compared to the commonly used Shono's protocol, which in our hands led to partial racemization of the endocyclic enecarbamate 18c.

Electroorganic Chemistry. 60. Electroorganic Synthesis of Enamides and Enecarbamates and Their Utilization in Organic Synthesis.

A variety of enecarbamates and enamides were synthesized from α-methoxy carbamates and α-methoxy amides prepared by anodic methoxylation of amine derivatives.Some new carbon-carbon bond-forming reactions and hydroxylation at the β position of amines have been accomplished by using these enecarbamates and enamides as key intermediates.Also, new synthetic routes of nicotinaldehyde and pyrrole derivatives have been exploited by utilizing anodic dimethoxylation of carbamates of piperidine and pyrrolidine, respectively.