63808-36-6

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-N-CBZ-2-CYANO-PYRROLIDINE is used as a chiral building block for the synthesis of various pharmaceuticals. Its specific stereochemistry and cyano group enable the creation of complex organic molecules that are essential in developing new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-1-N-CBZ-2-CYANO-PYRROLIDINE serves as a key intermediate in the production of agrochemicals. Its unique properties allow for the development of effective and targeted pesticides and other agricultural chemicals that can enhance crop protection and yield.
Used in Organic Synthesis:
(S)-1-N-CBZ-2-CYANO-PYRROLIDINE is utilized as a starting material in organic synthesis, where it contributes to the formation of a wide range of organic compounds. Its versatility and reactivity make it an important component in the synthesis of various complex molecules for different applications.
Used in Chemical Industry for Production of Other Important Chemicals:
As a key intermediate, (S)-1-N-CBZ-2-CYANO-PYRROLIDINE plays a crucial role in the chemical industry for the production of other important chemicals. Its properties facilitate the synthesis of a variety of compounds and materials that find use in multiple sectors, highlighting its significance in the broader chemical manufacturing process.

InChI:InChI=1/C13H14N2O2/c14-9-12-7-4-8-15(12)13(16)17-10-11-5-2-1-3-6-11/h1-3,5-6,12H,4,7-8,10H2/t12-/m0/s1

Upstream product

• 7531-52-4 L-prolinamide 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 
• 501-53-1 benzyl chloroformate 
• 147-85-3 L-proline 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 71461-30-8 (S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester 
• 34079-31-7 Z-Pro-NH₂ 

Downstream Products

• 140903-27-1 (S)-2-Ethylsulfanylcarbonimidoyl-pyrrolidine-1-carboxylic acid benzyl ester; hydrochloride 
• 133031-58-0 2-<(2S)-1-benzyloxycarbonyl-2-pyrrolidinyl>pyridine 
• 33876-20-9 5-<1-(benzyloxycarbonyl)pyrrolidin-2-yl>tetrazole 
• 33876-20-9 (2S)-2-(1H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 700875-99-6 (2S)-2-{(4S)-4-benzyl-4,5-dihydro-1,3-oxazol-2-yl}pyrrolidine-1-carboxylic acid benzyl ester 
• 700875-91-8 (2S)-2-{(4S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl}pyrrolidine-1-carboxylic acid benzyl ester 
• 96792-03-9 5-<1-<5(S)-benzamido-4-oxo-6-phenylhexanoyl>pyrrolidin-2-yl>tetrazole 
• 140903-29-3 N-(Benzyloxycarbonyl)-L-dithioprolin-ethylester 
• 140903-29-3 2-Ethylsulfanylthiocarbonyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 22083-78-9 2-<(2S)-2-pyrrolidinyl>pyridine 
• 68582-51-4 2-nicotine 
• 133031-59-1 2-<(2S)-1-benzyl-2-pyrrolidinyl>pyridine 
• 133031-60-4 2-<1-(α-methoxy-α-trifluoromethylphenylacetyl)-2-pyrrolidinyl>pyridine 
• 63815-23-6 2-ethoxycarbonimidoyl-pyrrolidine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Fast Cyclization of a Proline-Derived Self-Immolative Spacer Improves the Efficacy of Carbamate Prodrugs

Self-immolative (SI) spacers are sophisticated chemical constructs designed for molecular delivery or material degradation. We describe herein a (S)-2-(aminomethyl)pyrrolidine SI spacer that is able to release different types of anticancer drugs (possessing either a phenolic or secondary and tertiary hydroxyl groups) through a fast cyclization mechanism involving carbamate cleavage. The high efficiency of drug release obtained with this spacer was found to be beneficial for the in vitro cytotoxic activity of protease-sensitive prodrugs, compared with a commonly used spacer of the same class. These findings expand the repertoire of degradation machineries and are instrumental for the future development of highly efficient delivery platforms.

Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes

Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. We report a copper-hydride(CuH)-catalyzed process that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups, and can be performed using a simple ligand, inexpensive siloxanes, and low catalyst loading.

One-pot synthesis of orthogonally protected dipeptide selenazoles employing Nα-amino selenocarboxamides and α-bromomethyl ketones

A simple and efficient protocol for the synthesis of selenazole containing dipeptidomimetics using Nα-amino selenocarboxamides and α-bromomethyl ketones is described. All the compounds made were isolated in good yields and fully characterized.

Glycosylation mediated - BAIL in aqueous solution

The use of Br?nsted acid ionic liquid (BAIL) as a catalyst for the activation of unreactive and unprotected glycosyl donors has been demonstrated for the first time in aqueous solution.

Enantioselective total synthesis of (S)-(+)-lennoxamine through asymmetric hydrogenation mediated by l-proline-tetrazole ruthenium catalyst

A novel asymmetric synthetic strategy to prepare isoindolobenzazepine based lennoxamine alkaloid has been achieved in high ee% starting from 2-(benzo[d][1,3]dioxol-5-yl)ethanamine and 1-(chloromethyl)-2,3-dimethoxybenzene in 5 steps and with a 34% overall yield. The potentiality of this route involved the Bischler-Napieralsky cyclization that leads to tetracyclic indolinium skeleton, generation of chiral center through asymmetric hydrogen-transfer reaction employing l-proline-tetrazole as chiral ligand with Ru/Ir/Rh, and anodic oxidation as the key steps in the synthesis.

Pyrrolidine amides of pyrazolodihydropyrimidines as potent and selective KV1.5 blockers

Design and synthesis of pyrazolodihydropyrimidines as KV1.5 blockers led to the discovery of 7d as a potent and selective antagonist. This compound showed atrial selective prolongation of effective refractory period in rabbits and was selected for clinical development.

Synthesis of substituted 5-(pyrrolidin-2-yl)tetrazoles and their application in the asymmetric Biginelli reaction

A series of chiral substituted 5-(pyrrolidin-2-yl)tetrazoles have been synthesized and evaluated as organocatalysts for the asymmetric Biginelli reaction. The relationship between catalytic activity and the different catalyst structures is briefly discussed. By using the optimized catalyst C10 (10 mol-%), a series of 3,4-dihydropyrimidin-2(1H)-one (DHPM) derivatives have been obtained in 63-88% yields and 68-81 % ee values within 24 h at room temperature.

N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides

(Chemical Equation Presented) Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z′ = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.

Peptide deformylase inhibitors of Mycobacterium tuberculosis: Synthesis, structural investigations, and biological results

Bacterial peptide deformylase (PDF) belongs to a subfamily of metalloproteases catalyzing the removal of the N-terminal formyl group from newly synthesized proteins. We report the synthesis and biological activity of highly potent inhibitors of Mycobacterium tuberculosis (Mtb) PDF enzyme as well as the first X-ray crystal structure of Mtb PDF. Structure-activity relationship and crystallographic data clarified the structural requirements for high enzyme potency and cell based potency. Activities against single and multi-drug-resistant Mtb strains are also reported.