86953-80-2

Usage

General Description

The chemical 1-Pyrrolidinecarboxylicacid, 2-hydroxy-, methylester (9CI) is an organic compound with the molecular formula C6H11NO3. It is a methyl ester derivative of 2-hydroxy pyrrolidinecarboxylic acid, commonly known as proline. Proline is an important amino acid that plays a crucial role in protein synthesis and is essential for the proper functioning of the human body. The methyl ester form of proline is used in various pharmaceutical and chemical applications, including the synthesis of peptides and other bioactive compounds. 1-Pyrrolidinecarboxylicacid,2-hydroxy-,methylester(9CI) is also known for its potential use in the development of drugs and other therapeutic agents.

Upstream product

• 56475-80-0 N-(methoxycarbonyl)pyrrolidine 
• 56475-88-8 methyl 2-methoxypyrrolidine-1-carboxylate 
• 74761-41-4 (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 67-56-1 methanol 
• 762-72-1 allyl-trimethyl-silane 
• 1215765-14-2 1-chloro-2-oxopiperidin-3-yl acetate 
• 26407-91-0 methyl 2-oxopyrrolidine-1-carboxylate 

Downstream Products

• 1253522-80-3 1-benzyl-3-bromo-5-(1-(methoxycarbonyl)pyrrolidin-2-yl)pyridin-1-ium trifluoromethanesulfonate 
• 1253522-91-6 C₁₈H₂₁BrN₂O₃ 
• 1253522-82-5 3-bromo-1-(4-methoxybenzyl)-5-(1-(methoxycarbonyl)pyrrolidin-2-yl)pyridin-1-ium trifluoromethanesulfonate 
• 1253522-88-1 3-methoxy-1-(4-methoxybenzyl)-5-(1-(methoxycarbonyl)pyrrolidin-2-yl)pyridin-1-ium trifluoromethanesulfonate 
• 1253523-10-2 3-(1-(methoxycarbonyl)pyrrolidin-2-yl)-1-((S)-1-phenylethyl)pyridin-1-ium trifluoromethanesulfonate 
• 1253523-12-4 3,5-bis(1-(methoxycarbonyl)pyrrolidin-2-yl)-1-((S)-1-phenylethyl)pyridin-1-ium trifluoromethanesulfonate 

Relevant academic research and scientific papers

One-pot formation of piperidine- and pyrrolidine-substituted pyridinium salts via addition of 5-alkylaminopenta-2,4-dienals to N-acyliminium ions: Application to the synthesis of (±)-nicotine and analogs

Addition of 5-alkylaminopenta-2,4-dienals onto N-acyliminium ions, generated in situ from α-hydroxycarbamates derived from pyrrolidine or piperidine, in the presence of zinc triflate, followed by dehydrative cyclization, allowed the formation of pyridinium salts substituted at their 3-position by a five- or six-membered nitrogen heterocycle. Subsequent N-dealkylation of the pyridinium moiety and deprotection of the secondary amine or reduction of the carbamate function led to (±)-nicotine and analogs.

Photochemical rearrangement of N -chlorolactams: A route to N -heterocycles through concerted ring contraction

We report a novel ring contraction allowing the direct conversion of N-chlorolactams to their corresponding ring-contraction N-heterocycles upon photolysis. Results show that the rearrangement occurs with a variety of N-chlorolactams and that the greater the substitution at the migrating carbon, the greater the yield of product. Importantly, stereochemistry at the migrating carbon is conserved in the product. Rearranged products were isolated as their methyl carbamates in yields varying from 17% to 58%, with the major side product being the recyclable parent lactam.

Synthesis of 2,3-disubstituted pyrrolidines and piperidines via one-pot oxidative decarboxylation-β-iodination of amino acids

A new synthesis of 2,3-disubstituted pyrrolidines and piperidines is described. This mild procedure is based on the one-pot oxidative decarboxylation-β -iodination of α-amino acid carbamates or amides. The iodine is introduced at the previously unfunction

Tandem radical decarboxylation-oxidation of amino acids: A mild and efficient method for the generation of N-acyliminium ions and their nucleophilic trapping

A convenient methodology for the synthesis of 2-substituted pyrrolidines from α-amino acids is described. A number of cyclic and acyclic α-amino acid derivatives have been prepared in order to test the scope and diastereoselectivity of this method. These substrates were treated with iodosylbenzene or (diacetoxyiodo)benzene (DIB) and iodine in order to generate the corresponding carboxyl radical, which evolves by loss of carbon dioxide to produce a carbon radical which in turn undergoes oxidation to an N-acyliminium ion. This postulated intermediate could be trapped inter- or intramolecularly by oxygen, nitrogen and carbon nucleophiles. In the case of carbon nucleophiles, a Lewis acid is required for the concomitant carbon-carbon bond formation. High yields and modest diastereoselectivities were obtained. The present methodology was applied to the synthesis of ω-amino aldehydes or hemiaminals 8-14, 2-aminopyrrolidine derivative 15, aminolactone derivative 16, and azasugar analogues 17 and 18. When carbon nucleophiles were used, alkaloid precursors such as 2-allyl- or 2-alkylpyrrolidines 19-23 and 25 were obtained.

Tandem oxidative radical decarboxylation-β-iodination of amino acids. Application to the synthesis of chiral 2,3-disubstituted pyrrolidines

A mild and efficient procedure for the tandem decarboxylation- halogenation of α-amino acids is reported. The iodine is introduced at previously unfunctionalized positions, in good yields. The methodology has been used for the diastereoselective synthesis of 2,3-disubstituted pyrrolidines. (C) 2000 Elsevier Science Ltd.

Synthesis of alkaloids from amino acids via N-acyliminium ions generated by one-pot radical decarboxylation-oxidation

A one-pot methodology for the synthesis of α-substituted nitrogen heterocycles from commercial amino acids has been developed. Good stereoselectivity can be achieved with chiral substituted rings. This procedure has been applied to the synthesis of piperidine, pyrrolidine and indolizidinone alkaloids. (C) 2000 Elsevier Science Ltd.

Oxidative decarboxylation of α-amino acids: A mild and efficient method for the generation of N-acyliminium ions

The oxidative decarboxylation of α-amino acids using the system (diacetoxyiodo)benzene or iodosylbenzene and iodine proceeded smoothly at room temperature. The intermediacy of an N-acyliminium cation has been demonstrated through intermolecular and intram

Electroorganic Chemistry. Part 80. α-Hydroxylation of N-Acylated Cyclic Amines and Utilization of the Products as Amino Aldehyde Equivalents

A general method for the transformation of N-acylated cyclic amines (1) to amino aldehydes (4) was exploited.N-Benzoyl- or N-alkoxycarbonyl-α-methoxyamines (2) were prepared by anodic reaction of (1) in methanol.Treatment of (2) with dilute hydrochloric acid gave the corresponding α-hydroxylated compounds (3) which are amino aldehydes equivalents.The reaction of (3) with methoxycarbonylmethylenetriphenylphosphorane yielded ω-amino-α,β-unsaturated esters in satisfactory yields.

ACETOXYLATION OF PIPERIDINE DERIVATIVES AT THE 3-POSITION. STEREOSELECTIVE SYNTHESIS OF PSEUDOCONHYDRINE AND N-METHYLPSEUDOCONHYDRINE

Anodic oxidation of N-methoxycarbonylpipridine derivatives in AcOH gave 2,3-diacetoxylated products, which were shown to be useful intermediates for the stereoselective synthesis of 3-hydroxypiperidine derivatives including pseudoconhydrine and N-methylpseudoconhydrine, the Conium alcaloids.

Palladium-Catalyzed Carbonylation. A New Synthesis of α-Methylene γ-, δ-, and ε-Lactams and -Lactones Including Bicyclic Lactams of Pyrrolizidine and Indolizidine Skeletons

The insertion of carbon monoxide into vinyl halides bearing the secondary amine or alcohol with a catalytic amount of Pd(OAc)2 and PPh3 was realized to give five-, six-, and seven-membered lactams and lactones carrying α-methylene groups in fairly good yields.Bicyclic heterocycles, pyrrolizidine and indolizidine derivatives, were also synthesized from pyrrolidine and piperidine derivatives possessing vinyl halide groups in the side chain at the 2-position of the ring by means of palladium-catalyzed carbonylation.