3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cis-

Base Information

• Chemical Name: 3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cis-
• CAS No.: 82959-87-3
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.257
• Mol file: 82959-87-3.mol

Synonyms:CIS-2-PHENYL-PYRROLIDINE-3-CARBOXYLIC ACID METHYL ESTER;3-Pyrrolidinecarboxylic acid,2-phenyl-,methyl ester,cis-;(2S,3R)-2-phenylpyrrolidine-3-carboxylic acid;METHYL 2-PHENYLPYRROLIDINE-3-CARBOXYLATE;3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cis-;

Chemical Property of 3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cis-

Chemical Property:

• PSA: 38.33000
• LogP: 1.83900

Purity/Quality:

98%min ^*data from raw suppliers

Methylcis-2-Phenyl-3-pyrrolidinecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cis-

There total 26 articles about 3-Pyrrolidinecarboxylic acid, 2-phenyl-, methyl ester, cis- 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: 91.0%

C13H14N2O2 → cis-3-(methoxycarbonyl)-2-phenylpyrrolidine (82959-87-3,82959-88-4,95683-62-8)

Guidance literature:

C₁₃H₁₄N₂O₂; With borane-THF; In tetrahydrofuran; at 20 ℃; for 0.25h; Inert atmosphere;

With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

With palladium 10% on activated carbon; In methanol; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1002/anie.201500961

Reference yield: 91.0%

C13H17BN2O2 → cis-3-(methoxycarbonyl)-2-phenylpyrrolidine (82959-87-3,82959-88-4,95683-62-8)

Guidance literature:

C₁₃H₁₇BN₂O₂; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

With C₁₃H₁₇BN₂O₂; In tetrahydrofuran; for 0.5h;

DOI:10.1002/anie.201500961

Reference yield: 83.0%

N-<(trimethylsilyl)methyl>benzaldimine (57402-97-8) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (R)-2-Phenyl-pyrrolidine-3-carboxylic acid methyl ester (82959-87-3,82959-88-4,95683-62-8)

Guidance literature:

With cesium fluoride; trimethylsilyl trifluoromethanesulfonate; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 60 - 65 ℃; for 20h;

DOI:10.1016/S0040-4039(00)87403-1

upstream raw materials:

N-<(trimethylsilyl)methyl>benzaldimine

acrylic acid methyl ester

n-Butyl chloride

(E)-N-(phenylmethylene)-1-(trimethylsilyl)methylamine

Downstream raw materials:

(2S,3S)-1-Benzoyl-2-phenyl-pyrrolidine-3-carboxylic acid methyl ester

(2S,3R)-1-Benzoyl-2-phenyl-pyrrolidine-3-carboxylic acid methyl ester

Refernces

• 1、 Li, Jundong,Lin, Na,Yu, Lei,Zhang, Yandong. "Synthesis of β-prolinols via [3+2] cycloaddition and one-pot programmed reduction: Valuable building blocks for polyheterocycles". supporting information. p. 5777 - 5780. Retrieved 2016/12/06.
• 2、 Li, Jundong,Zhao, Huaibo,Jiang, Xunjin,Wang, Xiance,Hu, Haiming,Yu, Lei,Zhang, Yandong. "The Cyano Group as a Traceless Activation Group for the Intermolecular [3+2] Cycloaddition of Azomethine Ylides: A Five-Step Synthesis of (±)-Isoretronecanol". supporting information. p. 6306 - 6310. Retrieved 2015/05/20.