185057-50-5

Basic information

• Product Name: N-Cbz-3-aminopyrrolidine
• Synonyms: BENZYL 3-AMINOPYRROLIDINE-1-CARBOXYLATE;1-N-CBZ-3-AMINO-PYRROLIDINE;1-CBZ-3-AMINO PYRROLIDINE;3-AMINO-PYRROLIDINE-1-CARBOXYLIC ACID BENZYL ESTER;3-AMINO-1-N-CBZ-PYRROLIDINE;N-Cbz-3-aminopyrrolidine;1-Benzyloxycarbonyl-3-aminopyrrolidine, 97%;1-cbz-3-aminopyrrolidine HCl or 1-benzyloxycarbonyl-3-aminopyrrolidine HCl
• CAS NO: 185057-50-5
• Molecular Formula: C₁₂H₁₆N₂O₂
• Molecular Weight: 220.27
• Product Categories: Amines;Pyrrolidines;Pyrrole&Pyrrolidine&Pyrroline
• Mol File: 185057-50-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 351.7 °C at 760 mmHg
• Flash Point: 166.5 °C
• Appearance: /
• Density: 1.186 g/cm³
• Vapor Pressure: 4.04E-05mmHg at 25°C
• Refractive Index: 1.5485
• PKA: 9.52±0.20(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: N-Cbz-3-aminopyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-3-aminopyrrolidine(185057-50-5)
• EPA Substance Registry System: N-Cbz-3-aminopyrrolidine(185057-50-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 185057-50-5(Hazardous Substances Data)

Usage

Description

N-Cbz-3-aminopyrrolidine is a versatile chemical compound that features a pyrrolidine ring with an attached amino group and a carbobenzyloxy (Cbz) protecting group. N-Cbz-3-aminopyrrolidine is widely recognized for its utility in organic synthesis, where it serves as a fundamental building block for the creation of a diverse array of compounds. The Cbz group plays a crucial role in protecting the amino group's reactivity during chemical reactions, ensuring that it can be selectively removed at a later stage to facilitate the formation of specific products. Its applications extend across various fields, including medicinal chemistry for the synthesis of potential drug candidates and the development of a broad spectrum of organic molecules.

Uses

Used in Organic Synthesis:
N-Cbz-3-aminopyrrolidine is used as a building block for the synthesis of various organic compounds due to its ability to be selectively deprotected and incorporated into complex molecular structures.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, N-Cbz-3-aminopyrrolidine is utilized as a key intermediate in the synthesis of potential drug candidates, leveraging its reactivity and the strategic use of the Cbz protecting group to access specific pharmaceutically relevant molecules.
Used in the Development of Organic Molecules:
N-Cbz-3-aminopyrrolidine is employed in the development of a wide range of organic molecules, showcasing its adaptability and value in synthetic chemistry for creating compounds with diverse applications and properties.

InChI:InChI=1/C12H16N2O2/c13-11-6-7-14(8-11)12(15)16-9-10-4-2-1-3-5-10/h1-5,11H,6-9,13H2

Upstream product

• 68471-57-8 2,3-dihydro-pyrrole-1-carboxylic acid benzyl ester 
• 79286-79-6 pyrrolidin-3-amine 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 122536-73-6 benzyl (R)-3-amino-pyrrolidine-1-carboxylate 
• 185057-49-2 (S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinecarboxylic acid,phenylmethyl ester 
• 140412-80-2 3-((S)-2-tert-Butoxycarbonylamino-propionylamino)-pyrrolidine-1-carboxylic acid benzyl ester 
• 140412-80-2 3-((R)-2-tert-Butoxycarbonylamino-propionylamino)-pyrrolidine-1-carboxylic acid benzyl ester 

Relevant articles and documents

Design, synthesis and SAR of antitubercular benzylpiperazine ureas

Abstract: N-furfuryl piperazine ureas disclosed by scientists at GSK Tres Cantos were chosen as antimycobacterial hits from a phenotypic whole-cell screen. Bioisosteric replacement of the furan ring in the GSK Tres Cantos molecules with a phenyl ring led to molecule (I) with an MIC of 1?μM against Mtb H37Rv, low cellular toxicity (HepG2 IC50 ~ 80?μM), good DMPK properties and specificity for Mtb. With the aim of delineating the SAR associated with (I), fifty-five analogs were synthesized and screened against Mtb. The SAR suggests that the piperazine ring, benzyl urea and piperonyl moieties are essential signatures of this series. Active compounds in this series are metabolically stable, have low cellular toxicity and are valuable leads for optimization. Molecular docking suggests these molecules occupy the Q0 site of QcrB like Q203. Graphic Abstract: Bioisosteric replacement of N-furfuryl piperazine-1-carboxamides yielded molecule (I) a novel lead with satisfactory PD, metabolism, and toxicity profiles.[Figure not available: see fulltext.]

AMIDE DERIVATIVE

The present invention relates to a compound of the formula (I) being useful as a renin inhibitor, or a pharmaceutically acceptable salt thereof. wherein R1a is a hydrogen atom, an optionally substituted C1-6 alkyl, etc.; R1b is an optionally substituted C1-6 alkoxy, etc.; R1c is a hydrogen atom, an optionally substituted C1-6 alkoxy, etc.; R2 is a hydrogen atom, an optionally substituted C1-6 alkyl, etc.; R3a, R3b, R3c and R3d are independently the same or different, and each is a group of the formula: -A-B (in which A is a single bond, -(CH2)sO-, - (CH2)sN(R4)CO-, etc., B is a hydrogen atom, an optionally substituted C1-6 alkyl, etc.), etc.; R4 is a hydrogen atom, an optionally substituted C1-6 alkyl, etc.; s is 0, etc.; and n is 1, etc.