63808-36-6

Basic information

• Product Name: (S)-1-N-CBZ-2-CYANO-PYRROLIDINE
• Synonyms: 1-Pyrrolidinecarboxylic acid, 2-cyano-, phenylmethyl ester, (2S)-;(S)-1-Cbz-2-cyanopyrrolidine
• CAS NO: 63808-36-6
• Molecular Formula: C₁₃H₁₄N₂O₂
• Molecular Weight: 230.266
• Mol File: 63808-36-6.mol
• Article Data: 21

Chemical Properties

• Melting Point: 37-39 °C
• Boiling Point: 403.618 °C at 760 mmHg
• Flash Point: 197.902 °C
• Appearance: /
• Density: 1.208 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: 2-8°C
• PKA: -5.02±0.40(Predicted)
• CAS DataBase Reference: (S)-1-N-CBZ-2-CYANO-PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-N-CBZ-2-CYANO-PYRROLIDINE(63808-36-6)
• EPA Substance Registry System: (S)-1-N-CBZ-2-CYANO-PYRROLIDINE(63808-36-6)

Safety Data

• Hazardous Substances Data: 63808-36-6(Hazardous Substances Data)

Usage

General Description

(S)-1-N-CBZ-2-CYANO-PYRROLIDINE is a chemical compound with the molecular formula C14H16N2O2. It is a derivative of pyrrolidine and is commonly used in organic synthesis as a chiral building block. The compound is often used as a starting material for the synthesis of various pharmaceuticals and agrochemicals. It is also used as a key intermediate in the production of other important chemicals. The compound is characterized by its specific stereochemistry and cyano group, making it a valuable reagent in the synthesis of complex organic molecules. Its properties and versatility make it an important component in the chemical industry for the production of various compounds and materials.

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

• 33876-20-9 5-<1-(benzyloxycarbonyl)pyrrolidin-2-yl>tetrazole 
• 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 
• 944030-47-1 (S)-5-phenyl-2-(pyrrolidin-2-yl)-1H-imidazole 
• 871981-77-0 3-[5-(1-benzyloxycarbonyl-(2S)-pyrrolidinyl)-2H-tetrazol-2-yl]propionic acid ethyl ester 
• 119020-03-0 2-(S)-aminomethyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 63815-23-6 2-ethoxycarbonimidoyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 133031-60-4 2-<1-(α-methoxy-α-trifluoromethylphenylacetyl)-2-pyrrolidinyl>pyridine 
• 133031-59-1 2-<(2S)-1-benzyl-2-pyrrolidinyl>pyridine 
• 68582-51-4 2-nicotine 
• 22083-78-9 2-<(2S)-2-pyrrolidinyl>pyridine 

Relevant articles and documents

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.

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.

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.