938-54-5

Basic information

• Product Name: (S)-(-)-1-ETHYL-2-PYRROLIDINECARBOXYLIC ACID ETHYL ESTER
• Synonyms: (-)-1-ETHYL-L-PROLINE ETHYL ESTER;ETHYL (S)-(-)-1-ETHYL-2-PYRROLIDINECARBOXYLATE;(S)-(-)-1-ETHYL-2-PYRROLIDINECARBOXYLIC ACID ETHYL ESTER;(S)-(-)-1-ETHYLPROLINE ETHYL ESTER;Et-Pro-OEt;Ethyl 1-ethylprolinate;(S)-(-)-1-Ethyl-2-pyrrolidinecarboxylic Acid Ethyl Ester (-)-1-Ethyl-L-proline Ethyl Ester Et-Pro-OEt;1-ethyl-2-pyrrolidinecarboxylic acid ethyl ester
• CAS NO: 938-54-5
• Molecular Formula: C9H17NO2
• Molecular Weight: 171.24
• Product Categories: Amino Acid Ethyl Esters;Amino Acids;Amino Acids (C-Protected);Biochemistry;Chiral Building Blocks;Esters (Chiral);Synthetic Organic Chemistry
• Mol File: 938-54-5.mol

Chemical Properties

• Boiling Point: 209.367 °C at 760 mmHg
• Flash Point: 73.033 °C
• Appearance: /
• Density: 0.97
• Vapor Pressure: 0.204mmHg at 25°C
• Refractive Index: -94 ° (C=0.6, CHCl3)
• CAS DataBase Reference: (S)-(-)-1-ETHYL-2-PYRROLIDINECARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1-ETHYL-2-PYRROLIDINECARBOXYLIC ACID ETHYL ESTER(938-54-5)
• EPA Substance Registry System: (S)-(-)-1-ETHYL-2-PYRROLIDINECARBOXYLIC ACID ETHYL ESTER(938-54-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 938-54-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-(-)-1-Ethyl-2-pyrrolidinecarboxylic Acid Ethyl Ester is used as a building block for the synthesis of more complex organic molecules, contributing to the development of new compounds with potential applications in various industries.
Used in Pharmaceutical Research:
(S)-(-)-1-Ethyl-2-pyrrolidinecarboxylic Acid Ethyl Ester is used as an intermediate in the synthesis of pharmaceutical compounds, aiding in the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
(S)-(-)-1-Ethyl-2-pyrrolidinecarboxylic Acid Ethyl Ester is used as a research tool in chemical studies, helping scientists understand the properties and reactivity of this specific chiral compound and its potential applications in various chemical processes.
Used in Chemistry-Related Fields:
(S)-(-)-1-Ethyl-2-pyrrolidinecarboxylic Acid Ethyl Ester is used as a component in various chemistry-related fields, such as materials science, where its unique properties may contribute to the development of new materials with specific characteristics.

InChI:InChI=1/C9H17NO2/c1-3-10-7-5-6-8(10)9(11)12-4-2/h8H,3-7H2,1-2H3/t8-/m0/s1

Upstream product

• 54288-59-4 diethyl 2-bromo-2-(3-bromopropyl)malonate 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 
• 23037-82-3 (S)-ethyl 1-acetylpyrrolidine-2-carboxylate 
• 74-96-4 ethyl bromide 
• 147-85-3 L-proline 
• 75-03-6 ethyl iodide 
• 101738-88-9 1-ethyl-pyrrolidine-2,2-dicarboxylic acid diethyl ester 
• 98435-76-8 1-ethylpyrrolidine-2-carboxylic acid 

Downstream Products

• 22795-99-9 (S)-2-(Aminomethyl)-1-ethylpyrrolidine 
• 114812-34-9 (-)-(S)-1-ethyl-2-pyrrolidinecarboxamide 
• 3433-34-9 1-ethyl-2-hydroxymethylpyrrolidine 
• 107599-39-3 (S)-1-Ethyl-pyrrolidine-2-carboxylic acid dimethylamide 
• 107599-38-2 (S)-1-Ethyl-pyrrolidine-2-carboxylic acid methylamide 

Relevant articles and documents

Selective Rhodium-Catalyzed Reduction of Tertiary Amides in Amino Acid Esters and Peptides

Efficient reduction of the tertiary amide bond in amino acid derivatives and peptides is described. Functional group selectivity has been achieved by applying a commercially available rhodium precursor and bis(diphenylphosphino)propane (dppp) ligand together with phenyl silane as a reductant. This methodology allows for specific reductive derivatization of biologically interesting peptides and offers straightforward access to a variety of novel peptide derivatives for chemical biology studies and potential pharmaceutical applications. The catalytic system tolerates a variety of functional groups including secondary amides, ester, nitrile, thiomethyl, and hydroxy groups. This convenient hydrosilylation reaction proceeds at ambient conditions and is operationally safe because no air-sensitive reagents or highly reactive metal hydrides are needed.

An experimental and computational study of stereoselectivity and reactivity in Lewis acid promoted lithiation-substitution of tertiary amines

Reaction of BF3 coordinated N-ethylpyrrolidine with benzophenone, using a preformed complex of s-BuLi and (-)-sparteine for lithiation at -78 °C, affords enantio-enriched R-product (er 85:15). With a warm-cool cycle (-78° → 0°, 2 h, → -78°) pri

EFFICIENT STEREOCONSERVATIVE SYNTHESIS OF 1-SUBSTITUTED (S)- AND (R)-2-AMINOMETHYLPYRROLIDINES AND INTERMEDIATES THERETO

Stereoconservative method for preparation of an (R)- or (S)-isomer of the compound of the formula I with at least 95% optical purity wherein R1 is a hydrogen atom, a saturated or unsaturated lower alkyl group, a cycloalkyl group, or a group (CH2)m Ph wherein m is 0-3 and Ph is a substituted or unsubstituted phenyl group including 1) O,N-dialkylation, directly or stepwise of (R)- or (S)-proline 2) aminolysis 3) reduction to formation of the (R)- or (S)-isomer of the compound of the formula I, and new intermediates II and III in optical active form obtained by the reaction steps above and wherein R2 is defined as R1 above.

Efficient Stereoconservative Syntheses of 1-Substituted (S)- and (R)-2-Aminomethylpyrrolidines

Three-step stereoconservative syntheses of chiral 1-substituted 2-aminomethylpyrrolidines with high optical purities from D- or L-proline are described.The key intermediates, 1-substituted prolinamides, were obtained by N,O-dialkylation of proline followed by ammonolysis or by 1-alkylation of prolinamide.Reduction furnished the optically pure (about 99percent e.e.) pyrrolidine derivatives, which are useful as intermediates in the preparation of antipsychotic substituted benzamides.