trans-3-Phenyl-D-proline

Base Information

• Chemical Name: trans-3-Phenyl-D-proline
• CAS No.: 118758-50-2
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.23
• DSSTox Substance ID: DTXSID60426262
• Mol file: 118758-50-2.mol

Synonyms:trans-3-Phenyl-D-proline;118758-50-2;(2R,3S)-3-Phenylpyrrolidine-2-carboxylic acid;trans-3-Phenylpyrrolidine-2-carboxylic acid;51212-37-4;DTXSID60426262;MFCD15071513;AKOS006323117;AC-22414;CS-0199924;(2R,3S)-3-Phenylpyrrolidine-2-carboxylicacid;EN300-1273054;J-003882;rac-(2R,3S)-3-phenylpyrrolidine-2-carboxylic acid;rel-(2R,3S)-3-Phenylpyrrolidine-2-carboxylic acid (H-Pro(3-Ph)-OH)

Chemical Property of trans-3-Phenyl-D-proline

Chemical Property:

• PSA: 49.33000
• LogP: 1.54550
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 211

Purity/Quality:

98%min ^*data from raw suppliers

(2R,3S)-3-PHENYL-PYRROLIDINE-2-CARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(C1C2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1CN[C@H]([C@@H]1C2=CC=CC=C2)C(=O)O

Technology Process of trans-3-Phenyl-D-proline

There total 2 articles about trans-3-Phenyl-D-proline 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:

(2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid (1000870-85-8) → trans-3-phenyl-(R)-proline (118758-50-2)

Guidance literature:

With hydrogenchloride; In acetic acid; for 18h; Heating;

DOI:10.1016/j.tetlet.2007.10.028

Reference yield:

(E)-3-phenylpropenal (14371-10-9) → trans-3-phenyl-(R)-proline (118758-50-2)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; triethylamine; Yield given. Multistep reaction; 1.) methanol, 60 deg C, 72 h; 2.) methanol, 80 deg C; 3.) methanol, r.t., 24 h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + trans-3-phenyl-(R)-proline (118758-50-2) → (2R,3S)-1-(tert-butoxycarbonyl)-3-phenylpyrrolidine-2-carboxylic acid (123724-32-3,210420-48-7,149252-59-5)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 22h;

DOI:10.1016/j.tetlet.2007.10.028

upstream raw materials:

(E)-3-phenylpropenal

(2R,3S)-1-Acetyl-3-phenyl-pyrrolidine-2-carboxylic acid

Downstream raw materials:

(2R,3S)-1-(tert-butoxycarbonyl)-3-phenylpyrrolidine-2-carboxylic acid

Refernces

• 1、 Belokon', Yuri N.,Bulychev, Aleksandr G.,Pavlov, Viacheslav A.,Fedorova, Eugenia B.,Tsyryapkin, Vladimir A.,et al.. "Synthesis of Enantio- and Diastereoiso-merically Pure Substituted Prolines via Condensation of Glycine with Olefins Activated by a Carbonyl Group". . p. 2075 - 2084. Retrieved 2007/10/02.