(4R)-1-N-Boc-4-Benzyl-D-proline

Base Information

• Chemical Name: (4R)-1-N-Boc-4-Benzyl-D-proline
• CAS No.: 158459-13-3
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• DSSTox Substance ID: DTXSID50428038
• Wikidata: Q82240810
• Mol file: 158459-13-3.mol

Synonyms:(4R)-1-N-Boc-4-Benzyl-D-proline;158459-13-3;(2R,4R)-4-benzyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;(2R,4R)-4-Benzyl-1-(tert-Butoxycarbonyl)pyrrolidine-2-carboxylicacid;(2R,4R)-4-BENZYL-1-(TERT-BUTOXYCARBONYL)PYRROLIDINE-2-CARBOXYLIC ACID;(2R,4R)-4-Benzyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;SCHEMBL21409001;DTXSID50428038;MFCD07784046;AS-36766;CS-0171722;CS-0356544;(2R,4R)-4-benzyl-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid;rel-1-(1,1-Dimethylethyl) (2R,4R)-4-(phenylmethyl)-1,2-pyrrolidinedicarboxylate

Chemical Property of (4R)-1-N-Boc-4-Benzyl-D-proline

Chemical Property:

• Vapor Pressure: 8.32E-09mmHg at 25°C
• Refractive Index: 1.55
• Boiling Point: 447.9°Cat760mmHg
• Flash Point: 224.7°C
• PSA: 66.84000
• Density: 1.185g/cm³
• LogP: 2.87720
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 305.16270821
• Heavy Atom Count: 22
• Complexity: 409

Purity/Quality:

>96% ^*data from raw suppliers

(2R,4R)-4-Benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)CC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@@H]1C(=O)O)CC2=CC=CC=C2

Technology Process of (4R)-1-N-Boc-4-Benzyl-D-proline

There total 36 articles about (4R)-1-N-Boc-4-Benzyl-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: 92.0%

ethyl (2S,4S)-N-BOC-4-benzylprolinate (170947-82-7) → (2S,4S)-4-benzyl-N-tert-butyloxycarbonylproline (83623-78-3,158459-13-3)

Guidance literature:

With lithium hydroxide; In methanol; at 20 ℃; for 18h;

DOI:10.1016/j.bmcl.2005.03.120

Reference yield: 92.0%

ethyl (2S,4R)-N-BOC-4-benzylprolinate (171038-43-0) → (2S,4R)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (153074-95-4,158459-13-3)

Guidance literature:

With lithium hydroxide; In methanol; at 20 ℃; for 18h;

DOI:10.1016/j.bmcl.2005.03.120

Reference yield: 91.0%

2-benzyl 1-(tert-butyl) (2R,4S)-4-benzylpyrrolidine-1,2-dicarboxylate → (2R,4S)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1229439-64-8,158459-13-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 3h; under 760.051 Torr; Inert atmosphere;

upstream raw materials:

(2S,4R)-N-tert-butyloxycarbonyl-4-benzyl-2-hydroxymethylpyrrolidine

ethyl (2S,4S)-N-BOC-4-benzylprolinate

ethyl (2S,4R)-N-BOC-4-benzylprolinate

di-tert-butyl dicarbonate

Refernces

• 1、 Ibrahim, Mohamed A.,Johnson, Henry W. B.,Jeong, Joon Won,Lewis, Gary L.,Shi, Xian,Noguchi, Robin T.,Williams, Matthew,Leahy, James W.,Nuss, John M.,Woolfrey, John,Banica, Monica,Bentzien, Frauke,Chou, Yu-Chien,Gibson, Anna,Heald, Nathan,Lamb, Peter,Mattheakis, Larry,Matthews, David,Shipway, Aaron,Wu, Xiang,Zhang, Wentao,Zhou, Sihong,Shankar, Geetha. "Discovery of a novel class of potent and orally bioavailable sphingosine 1-phosphate receptor 1 antagonists". . p. 1368 - 1381. Retrieved 2012/04/04.
• 2、 Tian, Xinrong,Field, Timothy,Mazur, Adam W.,Ebetino, Frank H.,Wos, John A.,Crossdoersen, Doreen,Pinney, Beth B.,Sheldon, Russell J.. "Design, synthesis, and evaluation of proline based melanocortin receptor ligands". . p. 2819 - 2823. Retrieved 2007/10/03.