31795-93-4

Basic information

• Product Name: N-BENZYL-L-PROLINE
• Synonyms: (S)-1-N-(benzyl)-L-proline;(2S)-1-Benzylpyrrolidin-2-ylcarboxylic Acid;(S)-Benzylproline;1-(PhenylMethyl)-L-proline;1-(phenylnethyl)-L-proline;L-Proline, 1-(phenylmethyl)-;1-(benzyl)-L-proline;(S)-Benzyl-pyrrolidine-2-carboxylic acid
• CAS NO: 31795-93-4
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.25
• Product Categories: pharmacetical;Amino Acid Derivatives;Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Chiral Reagents
• Mol File: 31795-93-4.mol
• Article Data: 31

Chemical Properties

• Melting Point: 168-171°C
• Boiling Point: 343.1 °C at 760 mmHg
• Flash Point: 161.3 °C
• Appearance: white solid
• Density: 1.205
• Vapor Pressure: 2.76E-05mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Store at 0-5°C
• Solubility: Acetone (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• PKA: 2.35±0.20(Predicted)
• CAS DataBase Reference: N-BENZYL-L-PROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYL-L-PROLINE(31795-93-4)
• EPA Substance Registry System: N-BENZYL-L-PROLINE(31795-93-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 31795-93-4(Hazardous Substances Data)

Usage

Description

N-Benzyl-L-Proline is a white solid that serves as a reagent for the synthesis of optically pure α-amino-acids. It is an essential component in the production of various pharmaceuticals and bioactive compounds due to its unique chemical properties and structure.

Uses

Used in Pharmaceutical Industry:
N-Benzyl-L-Proline is used as a reagent for the synthesis of optically pure α-amino-acids, which are crucial building blocks for the development of various pharmaceuticals. Its ability to produce optically pure compounds ensures the desired biological activity and therapeutic effects of the final drug product.
Used in Bioactive Compounds Synthesis:
N-Benzyl-L-Proline is also used as a reagent in the synthesis of bioactive compounds, such as peptides, proteins, and other biologically relevant molecules. Its unique structure allows for the creation of novel compounds with potential applications in research, medicine, and other industries.

InChI:InChI=1/C12H15NO2/c14-12(15)11-7-4-8-13(11)9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,14,15)/t11-/m0/s1

Upstream product

• 147-85-3 L-proline 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 90741-31-4 (S)-N-benzyl-5-thioxoproline tert-butyl ester 
• 100-52-7 benzaldehyde 
• 170642-58-7 (S)-N-benzylproline tert-butyl ester 
• 955-40-8 N-benzyl-L-proline ethyl ester 
• 100-44-7 benzyl chloride 
• 71989-31-6 Fmoc-Pro-OH 
• 83528-04-5 (S)-N-benzyl-O-benzylpyrrolidine-2-carboxylate 

Downstream Products

• 138052-86-5 (S)-1-(1-benzylpyrrolidin-2-yl)ethanone 
• 96293-17-3 (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide 
• 105099-19-2 N-benzyl-(S)-proline chloroanhydride 
• 92086-93-6 (S)-1-benzylpyrrolidine-2-carboxylic acid hydrochloride 
• 113304-84-0 N-benzyl-(S)-proline methyl ester 
• 211805-51-5 (S)-1-Benzyl-pyrrolidine-2-carboxylic acid ((S)-1-benzyl-pyrrolidin-2-ylmethyl)-amide 
• 211805-57-1 (S)-1-Benzyl-pyrrolidine-2-carboxylic acid bis-((S)-1-benzyl-pyrrolidin-2-ylmethyl)-amide 
• 384333-96-4 N,N'-bis[2(S)-2-pyrrolidinylmethyl]phenylenediamine 
• 479677-97-9 N,N'-bis[(S)-N-benzylprolyl]-N-(2-aminoethyl-3-aminopropyl)triethoxysilylethylenediamine 
• 151264-96-9 1-benzyl-pyrrolidine-2-carboxylic acid tert-butylamide 

Relevant articles and documents

Conformational analysis and mu-opioid receptor affinity of short peptides, endomorphin models in a low polarity solvent.

Peptide carbamates containing the sequence H-Pro-Trp-PheNH2 showed in CDCl3 restricted conformations stabilized by the presence of a gamma-turn. To test the reliability of the peptides as endomorphin conformational models, we measured the affinities for mu-receptors labelled with [3H]-DAMGO. In particular, Cbz-Pro-Trp-PheNH2 displayed a nanomolar affinity.

Improved synthesis of proline-derived Ni(II) complexes of glycine: Versatile chiral equivalents of nucleophilic glycine for general asymmetric synthesis of α-amino acids

A synthetically practical and operationally convenient method for preparing (S)-2-[N-(N′-benzylprolyl)-amino]benzophenone (BPBP) and hitherto unknown (S)-2-[N-(N′-benzylprolyl)amino]-4-methylbenzophenone (4-Me-BPBP), (S)-2-[N-(N′-benzylprolyl)amino]-5-nitrobenzophenone (5-NO2-BPBP), and their corresponding Ni(II) complexes with glycine [GlyNi(II)BPBP], a widely used chiral equivalent of nucleophilic glycine, and new analogues [GlyNi(II)-4-Me-BPBP] and [GlyNi(II)-5-NO2-BPBP] is described. The key step of the method is the synthetically efficient amid bond formation between the corresponding o-aminobenzophenones, featuring significant steric shielding and low nucleophilicity of the amino functionality as well as sterically constrained (S)-N-benzylproline (BP).

Preparation of labeled aromatic amino acids: Via late-stage18F-fluorination of chiral nickel and copper complexes

A general protocol for the preparation of 18F-labeled AAAs and α-methyl-AAAs applying alcohol-enhanced Cu-mediated radiofluorination of Bpin-substituted chiral complexes using Ni/Cu-BPX templates as double protecting groups is reported. The chiral auxiliaries are easily accessible from commercially available starting materials in a few synthetic steps. The versatility of the method was demonstrated by the high-yielding preparation of a series of [18F]F-AAAs and the successful implementation of the protocol into automated radiosynthesis modules. This journal is

Catalytic Transfer Hydrodebenzylation with Low Palladium Loading

A highly-efficient catalytic system for hydrodebenzylation reaction is described. The cleavage of O-benzyl and N-benzyl protecting groups was performed using an uncommonly low palladium loading (0.02–0.3 mol%; TON up to 5000) in a relatively short reaction time. The approach was used for a variety of substrates including pharmaceutically important precursors, and gram-scale deprotection reaction was shown. Transfer conditions together with easy-to-make Pd/C catalyst are the key features of this debenzylation scheme. (Figure presented.).