(2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate
• CAS No.: 166941-66-8
• Molecular Formula: C13H17NO2
• Molecular Weight: 219.282
• DSSTox Substance ID: DTXSID60438926
• Nikkaji Number: J680.901D
• Mol file: 166941-66-8.mol

Synonyms:166941-66-8;(2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate;ethyl (2S,5S)-5-phenylpyrrolidine-2-carboxylate;L-Proline, 5-phenyl-, ethyl ester, (5S)-;SCHEMBL3600450;DTXSID60438926;AKOS016015875;A3700;CS-0055809;EN300-359583;EN300-370222;rac-ethyl (2R,5R)-5-phenylpyrrolidine-2-carboxylate;5beta-Phenylpyrrolidine-2alpha-carboxylic acid ethyl ester

Chemical Property of (2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.00035mmHg at 25°C
• Refractive Index: 1.52
• Boiling Point: 318.9 °C at 760 mmHg
• Flash Point: 146.7 °C
• PSA: 38.33000
• Density: 1.079g/cm³
• LogP: 2.37160
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 219.125928785
• Heavy Atom Count: 16
• Complexity: 236

Purity/Quality:

99% ^*data from raw suppliers

(2S,5S)-ETHYL 5-PHENYLPYRROLIDINE-2-CARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCC(N1)C2=CC=CC=C2
• Isomeric SMILES: CCOC(=O)[C@@H]1CC[C@H](N1)C2=CC=CC=C2

Technology Process of (2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate

There total 6 articles about (2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 34.0%

C18H25NO4 (166941-71-5) → α-(S)-5-Ethoxycarbonyl-2-phenylpyrrolidine (166941-66-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1039/b611583g

Reference yield:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate (144978-35-8,144978-12-1,251924-83-1) → α-(S)-5-Ethoxycarbonyl-2-phenylpyrrolidine (166941-66-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1 M LiBEt₃H, 30percent H₂O₂ / tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) 0 deg C, 20 min

2: p-TsOH*H₂O / Ambient temperature

3: 1.) CuBr*Me₂S, 2.) BF₃*OEt₂ / 1.) ether, -40 deg C, 45 min, 2.) -78 deg C, 30 min; 15 min; -78 deg C to room temp., 3 h; room temp., 1 h

4: TFA / CH₂Cl₂ / Ambient temperature

With copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; dihydrogen peroxide; lithium triethylborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00121a020

Reference yield:

5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (194594-23-5) → α-(S)-5-Ethoxycarbonyl-2-phenylpyrrolidine (166941-66-8)

Guidance literature:

Multi-step reaction with 3 steps

1: p-TsOH*H₂O / Ambient temperature

2: 1.) CuBr*Me₂S, 2.) BF₃*OEt₂ / 1.) ether, -40 deg C, 45 min, 2.) -78 deg C, 30 min; 15 min; -78 deg C to room temp., 3 h; room temp., 1 h

3: TFA / CH₂Cl₂ / Ambient temperature

With copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00121a020

upstream raw materials:

5-Ethoxycarbonyl-2-phenyl-Δ¹-pyrroline

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

(2S)-1-t-butyl 2-ethyl 5-methoxypyrrolidine-1,2-dicarboxylate

Refernces

• 1、 Momotake, Atsuya,Togo, Hideo,Yokoyama, Masataka. "Convenient synthesis of C-aza-2,3-dideoxynucleosides". . p. 1193 - 1200. Retrieved 2007/10/03.