166941-66-8

Basic information

• Product Name: (2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate
• Synonyms: (2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate
• CAS NO: 166941-66-8
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.282
• Mol File: 166941-66-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 318.9 °C at 760 mmHg
• Flash Point: 146.7 °C
• Appearance: /
• Density: 1.079g/cm³
• Vapor Pressure: 0.00035mmHg at 25°C
• Refractive Index: 1.52
• CAS DataBase Reference: (2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate(166941-66-8)
• EPA Substance Registry System: (2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate(166941-66-8)

Safety Data

• Hazardous Substances Data: 166941-66-8(Hazardous Substances Data)

Usage

General Description

(2S,5S)-Ethyl 5-phenylpyrrolidine-2-carboxylate is a chemical compound with the molecular formula C14H19NO2. It is a pyrrolidine derivative, which is a class of heterocyclic organic compounds. This particular compound is chiral, as indicated by the (2S,5S) in its name, meaning it has two stereocenters and exists in two enantiomeric forms. It has a phenyl group attached to the pyrrolidine ring, and an ethyl ester group attached to the carboxylate group, making it a carboxylate ester. (2S,5S)-Ethyl 5-phenylpyrrolidine-2-carboxylate may have applications in pharmaceuticals, agrochemicals, and materials science due to its unique structure and potential biological activity.

InChI:InChI=1/C13H17NO2/c1-2-16-13(15)12-9-8-11(14-12)10-6-4-3-5-7-10/h3-7,11-12,14H,2,8-9H2,1H3/t11-,12-/m0/s1

Upstream product

• 952-27-2 5-Ethoxycarbonyl-2-phenyl-Δ¹-pyrroline 
• 166941-71-5 C₁₈H₂₅NO₄ 
• 194594-24-6 (2S)-1-t-butyl 2-ethyl 5-methoxypyrrolidine-1,2-dicarboxylate 
• 194594-23-5 5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 

Relevant articles and documents

Trans-2,5-Disubstituted pyrrolidines: Rapid stereocontrolled access from sulfones

A direct method for the reliable synthesis of trans-2,5-distributed pyrrolidines from pyroglutamic acid that was conducted at scale and without chromatographic purification of key intermediates was investigated. An analogous reaction involving the partial reduction of succinimides and displacement of the resulting lactol with benzenesulfinic acid yields sulfonyl pyrrolidinones. It was found that a highly diastereoselective and general approach to 2,5-difunctionalized pyrrolidines could be achieved by applying this strategy to the pyroglutamate system. The four step synthesis required no chromatographic purification of intermediates, where the product sulfone was readily purified by recrystallization and the sequence proceeded in 52% overall yield. The results show that such an approach would be of great importance for the preparation of substituted pyrrolidines in natural product systems.

Stereoselective Addition of Grignard-Derived Organocopper Reagents to N-Acyliminium Ions: Synthesis of Enantiopure 5- and 4,5-Substituted Prolinates

Alkylation of nonracemic N-acyliminium ions derived from proline and 4-substituted prolines has been extended to different types of Grignard-derived organocopper reagents.The reaction proceeds with high yield and stereoselectivity to yield 5-mono- and 4,5-disubstituted prolinates.The stereochemistry is controlled by the formation of a RCu-? complex intermediate between the N-acyliminium ion, the carbonyl group of the ester, and the copper species.