33876-20-9

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-(1H-tetrazol-5-yl)-, phenylmethyl ester, (2S)-
• Synonyms: (S)-2-(tetrazol-5-yl) pyrrolidine-1-carboxylic acid benzyl ester;(S)-2-(tetrazol-5-yl)pyrrolidine-1-carboxylic acid benzyl ester;5-[(2S)-1-(benzyloxycarbonyl)pyrrolidine-2-yl]tetrazole;(S)-2-(1H-tetrazol-5-yl)-pyrrolidin-1-carboxylic acid benzyl ester;(S)-2-(1H-tetrazol-5-yl)pyrrolydine-1-carboxylic acid benzyl ester;(S)-2-(1H-tetrazol-5-yl)pyrrolidine-1-carboxylic acid benzyl ester
• CAS NO: 33876-20-9
• Molecular Formula: C13H15N5O2
• Molecular Weight: 273.294
• Mol File: 33876-20-9.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-(1H-tetrazol-5-yl)-, phenylmethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-(1H-tetrazol-5-yl)-, phenylmethyl ester, (2S)-(33876-20-9)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-(1H-tetrazol-5-yl)-, phenylmethyl ester, (2S)-(33876-20-9)

Safety Data

• Hazardous Substances Data: 33876-20-9(Hazardous Substances Data)

Usage

Derivatives

Phenylmethyl ester derivative of 1-pyrrolidinecarboxylic acid and 1H-tetrazole-5-yl
The compound is formed by combining a phenylmethyl ester group with 1-pyrrolidinecarboxylic acid and 1H-tetrazole-5-yl.

Chiral compound

(2S)configuration
The compound has a non-superimposable mirror image, which indicates its chirality.

Pharmaceutical use

Building block for the synthesis of various drugs and bioactive compounds
The compound serves as an intermediate in the creation of pharmaceutical products and other biologically active substances.

Potential applications

Development of new medications for a range of therapeutic uses
The compound has the potential to be used in the creation of new drugs for treating various medical conditions.

Therapeutic uses

Cardiovascular disease, inflammation, and central nervous system disorders
The compound may be used in the development of medications targeting these specific health issues.

Upstream product

• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 
• 501-53-1 benzyl chloroformate 
• 33878-70-5 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 34079-31-7 Z-Pro-NH₂ 
• 63808-36-6 (2S)-2-cyanopyrrolidine-1-carboxylic acid benzyl ester 
• 71461-30-8 (S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester 
• 6216-63-3 N-Cbz-Prolinol 
• 147-85-3 L-proline 

Downstream Products

• 920748-44-3 (S)-2-(2-methyl-2H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 920748-45-4 (S)-2-(1-methyl-1H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 96792-03-9 5-<1-<5(S)-benzamido-4-oxo-6-phenylhexanoyl>pyrrolidin-2-yl>tetrazole 
• 871981-77-0 3-[5-(1-benzyloxycarbonyl-(2S)-pyrrolidinyl)-2H-tetrazol-2-yl]propionic acid ethyl ester 

Relevant articles and documents

Practical synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole, incorporating efficient protecting group removal by flow-reactor hydrogenolysis

A practical, safe, high-yielding and efficient synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole has been developed, which avoids the generation of ammonium azide in the cyclisation step and the use of a 9:1 acetic acid-water mixture as the solvent in the hydrogenation. The previously extended hydrogenolysis reaction time (three days) is now reduced to hours through the use of an H-Cube (a continuous-flow reactor employing a mixed hydrogen-liquid flow stream). Georg Thieme Verlag Stuttgart.

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.