25070-74-0

Basic information

• Product Name: 1-Cbz-pyrrolidine
• Synonyms: 1-Cbz-pyrrolidine;N-benzyloxycarbonyl pyrrolidine;Benzyl pyrrolidine-1-carboxylate;1-Pyrrolidinecarboxylic acid benzyl ester;N-Carbobenzyloxypyrrolidine
• CAS NO: 25070-74-0
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.253
• Mol File: 25070-74-0.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• Density: 1.152±0.06 g/cm3 (20 oC 760 Torr)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-Cbz-pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cbz-pyrrolidine(25070-74-0)
• EPA Substance Registry System: 1-Cbz-pyrrolidine(25070-74-0)

Safety Data

• Hazardous Substances Data: 25070-74-0(Hazardous Substances Data)

Usage

General Description

1-Carboxybenzyl Pyrrolidine, commonly known as 1-Cbz-pyrrolidine, is a chemical compound with the molecular formula C14H17NO2. Recognized for its stable, white crystalline nature, it is often utilized in various organic syntheses within laboratory settings. As a form of Cbz-protected amine, it serves as a crucial reactive intermediate in the production of various pharmaceuticals and bioactive molecules. It is recommended to handle it carefully due to its slight hazardous nature, which may cause skin and eye irritation upon exposure. The compound is also well-known for its stability towards acidic and basic hydrolysis until exposed to more extreme conditions.

Upstream product

• 123-75-1 pyrrolidine 
• 173300-87-3 1,3-Bis(benzyloxycarbonyl)imidazolidin-2-one 
• 173300-82-8 2-Thioxo-imidazolidine-1,3-dicarboxylic acid dibenzyl ester 
• 173300-84-0 1,3-Bis(benzyloxycarbonyl)-3,4,5,6-tetrahydropyrimidine-2-thione 
• 91806-74-5 3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester 
• 175854-39-4 1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane 
• 179186-51-7 toluene-4-sulfonic acid 4-benzyloxycarbonylamino-butyl ester 
• 101625-10-9 N-[(phenylmethoxy)carbonyl]-4-bromobutylamine 
• 10544-63-5 ethyl crotonate 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 31970-04-4 1-carboxybenzyl-3-pyrrolidine 
• 25070-76-2 benzyl diallylcarbamate 
• 6216-63-3 N-Cbz-Prolinol 
• 95656-88-5 benzyl 3-hydroxypyrrolidine-1-carboxylate 

Downstream Products

• 88001-42-7 benzyl 2-methoxypyrrolidine-1-carboxylate 
• 83487-23-4 N-carbobenzoxy-2,5-dimethoxypyrrolidine 
• 69261-54-7 1-(benzyloxycarbonyl)pyrrolidin-2-ol 
• 100858-33-1 (3R)-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester 
• 880461-84-7 2-(1-methoxycarbonyl-2-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 269068-46-4 (2S)-1-[5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carbonyl]-pyrrolidine-carboxylic Acid 
• 5105-78-2 4-(benzyloxycarbonylamino)butyric acid 
• 100858-32-0 (S)-3-hydroxy-1-pyrrolidinecarboxylic acid phenylmethyl ester 
• 119020-06-3 (±)-benzyl 2-cyanopyrrolidine-1-carboxylate 
• 106412-39-9 (2RS)-1-[(enzyloxy)carbonyl]-2-ethoxypyrrolidine 

Relevant articles and documents

Oxidations of pyrrolidines and piperidines to afford CH-functionalized isopropyl-1-carboxylate congeners

This article describes the action of iodine(III) reagents [diacetoxyiodobenzene, PhI(OAc)2, and iodosobenzene, (PhIO)n] in conjunction with TMSBr which act as functional bromine equivalents in unique oxidations of saturated, carbamate protected N-heterocycles. Interestingly, during this work, treatment of the same carbamates with molecular bromine alone afforded similar products, which were sequestered by the solvent methanol.

Carbamate Synthesis Using a Shelf-Stable and Renewable C1 Reactant

4-Propylcatechol carbonate is a shelf-stable, renewable C1 reactant. It is easily prepared from renewable 4-propylcatechol (derived from wood) and dimethyl carbonate (derived from CO2) using a reactive distillation system. In this work, the 4-propylcatechol carbonate is used for the two-step synthesis of carbamates under mild reaction conditions. In the first step, 4-propylcatechol carbonate is treated with an alcohol at 50–80 °C in the presence of a Lewis acid catalyst, such as Zn(OAc)2?2 H2O. With liquid alcohols, no solvent is used and with solid alcohols 2-methyltetrahydrofuran is used as solvent. In the second step, the alkyl 2-hydroxy-propylphenyl carbonate intermediates obtained react with amines at room temperature in 2-methyltetrahydrofuran, forming the target carbamates and the byproduct 4-propylcatechol, which can be recycled into a carbonate reactant.

C(sp3)?H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis

Inspired by the reaction mechanism of photo-induced DNA cleavage in nature, a C(sp3)?H cyanation reaction promoted by visible-light photoredox/phosphate hybrid catalysis was developed. Phosphate radicals, generated by one-electron photooxidation of phosphate salt, functioned as a hydrogen-atom-transfer catalyst to produce nucleophilic carbon radicals from C(sp3)?H bonds with a high bond-dissociation energy. The resulting carbon radicals were trapped by a cyano radical source (TsCN) to produce the C?H cyanation products. Due to the high functional-group tolerance and versatility of the cyano group, the reaction will be useful for realizing streamlined building block syntheses and late-stage functionalization of drug-like molecules.