50888-84-1

Basic information

• Product Name: BENZYL (S)-(-)-2-(1-PYRROLIDINYLCARBONYL)-1-PYRROLIDINECARBOXYLATE
• Synonyms: BENZYL (S)-(-)-2-(1-PYRROLIDINYLCARBONYL)-1-PYRROLIDINECARBOXYLATE;(S)-Benzyl 2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate
• CAS NO: 50888-84-1
• Molecular Formula: C₁₇H₂₂N₂O₃
• Molecular Weight: 302.37
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
• Mol File: 50888-84-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 132-135 °C(lit.)
• Boiling Point: 485.6°Cat760mmHg
• Flash Point: 247.5°C
• Appearance: /
• Density: 1.233g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: BENZYL (S)-(-)-2-(1-PYRROLIDINYLCARBONYL)-1-PYRROLIDINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL (S)-(-)-2-(1-PYRROLIDINYLCARBONYL)-1-PYRROLIDINECARBOXYLATE(50888-84-1)
• EPA Substance Registry System: BENZYL (S)-(-)-2-(1-PYRROLIDINYLCARBONYL)-1-PYRROLIDINECARBOXYLATE(50888-84-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 50888-84-1(Hazardous Substances Data)

Usage

Uses

Benzyl (S)-(?)-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinecarboxylate can be used as an intermediate in the preparation of:An organocatalyst, which is used in the Michael addition of cyclic ketones.Hydrazone-based?chiral auxiliary, which is used to prepare chiral ketones.

InChI:InChI=1/C17H22N2O3/c20-16(18-10-4-5-11-18)15-9-6-12-19(15)17(21)22-13-14-7-2-1-3-8-14/h1-3,7-8,15H,4-6,9-13H2/t15-/m0/s1

Upstream product

• 123-75-1 pyrrolidine 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 1532548-78-9 1-(prop-2-ene-1-sulfinyl)pyrrolidine 
• 1148-11-4 Z-D-proline 

Downstream Products

• 889866-98-2 (S)-2-[(S)-2-(Pyrrolidine-1-carbonyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carboxylic acid benzyl ester 
• 134591-58-5 benzyl (S)-2-[(pyrrolidin-1-yl)methyl]pyrrolidine-1-carboxylate 

Relevant articles and documents

Rational design of simple organocatalysts for the hsicl3 enantioselective reduction of (E)-n-(1-phenylethylidene)aniline

Prolinamides are well-known organocatalysts for the HSiCl3 reduction of imines; however, custom design of catalysts is based on trial-and-error experiments. In this work, we have used a combination of computational calculations and experimental work, including kinetic analyses, to properly understand this process and to design optimized catalysts for the benchmark (E)-N-(1-phenylethylidene)aniline. The best results have been obtained with the amide derived from 4-meth-oxyaniline and the N-pivaloyl protected proline, for which the catalyzed process is almost 600 times faster than the uncatalyzed one. Mechanistic studies reveal that the formation of the component supramolecular complex catalyst-HSiCl3-substrate, involving hydrogen bonding breaking and costly conformational changes in the prolinamide, is an important step in the overall process.

Investigation of a novel diamine based chiral auxiliary in the asymmetric alkylation of ketones

A novel chiral auxiliary containing a pyrrolidine ring has been utilised in the preparation of various chiral ketones with good to excellent enantioselectivities (up to 92%). It has been successfully employed in aldol and Michael reactions giving moderate to high selectivity.

Prolylprolinol-catalyzed asymmetric michael addition of aliphatic aldehydes to nitroalkenes

Several novel prolylprolinol catalysts have been designed and synthesized. This type of compound showed high catalytic efficiency on pro-moting the direct addition of unmodified aldehydes to nitroalkenes. Among the catalysts surveyed, the least bulky memb