(r)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester

Base Information

• Chemical Name: (r)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester
• CAS No.: 160706-62-7
• Molecular Formula: C14H17 N O4
• Molecular Weight: 263.293
• Hs Code.: 2933399090
• European Community (EC) Number: 675-915-7
• DSSTox Substance ID: DTXSID60353064
• Nikkaji Number: J2.484.796I
• Wikidata: Q72500360
• Mol file: 160706-62-7.mol

Synonyms:160706-62-7;(r)-piperidine-1,3-dicarboxylic acid 1-benzyl ester;(R)-1-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid;D-1-Cbz-Nipecotic acid;(r)-1-cbz-piperidine-3-carboxylic acid;(3R)-1-phenylmethoxycarbonylpiperidine-3-carboxylic acid;(3R)-1-[(benzyloxy)carbonyl]piperidine-3-carboxylic acid;MFCD04114972;(r)-1-benzyloxycarbonylnipecotic acid;(R)N-CBz nipecotic acid;SCHEMBL1933206;(R)-1-((Benzyloxy)carbonyl)piperidine-3-carboxylicacid;DTXSID60353064;AMY14573;AKOS015839347;CS-W005180;DS-12399;EN300-121306;(R)-piperidine-1,3-dicarboxylic acid 1-benzylester;(R)-Piperidine-1,3-dicarboxylic acid1-benzyl ester;Q-102985;(R)-1-(benzyloxycarbonyl)piperidine-3-carboxylic acid;(R)-1-(benzyloxycarbonyl)-piperidine-3-carboxylic acid;(3R)-1-(Benzyloxycarbonyl)piperidine-3alpha-carboxylic acid

Chemical Property of (r)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester

Chemical Property:

• Vapor Pressure: 1.16E-08mmHg at 25°C
• Refractive Index: 1.568
• Boiling Point: 443.9°C at 760 mmHg
• PKA: 4.48±0.20(Predicted)
• Flash Point: 222.3°C
• PSA: 66.84000
• Density: 1.265
• LogP: 2.05770
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 263.11575802
• Heavy Atom Count: 19
• Complexity: 325

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-1-((Benzyloxy)carbonyl)piperidine-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CN(C1)C(=O)OCC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1C[C@H](CN(C1)C(=O)OCC2=CC=CC=C2)C(=O)O

Technology Process of (r)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester

There total 4 articles about (r)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester 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: 95.0%

→ (R)-1-((benzyloxy)carbonyl)piperidine-3-carboxylic acid (160706-62-7)

Guidance literature:

Reference yield: 85.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (R)-3-piperidinecarboxylic acid ethyl ester (+)-tartrate (163343-71-3,83602-38-4) → (R)-1-((benzyloxy)carbonyl)piperidine-3-carboxylic acid (160706-62-7)

Guidance literature:

(R)-3-piperidinecarboxylic acid ethyl ester (+)-tartrate; With sodium hydroxide; In water; at 5 ℃;

N-(Benzyloxycarbonyloxy)succinimide; In tetrahydrofuran; water; at 5 - 20 ℃; for 1h;

With hydrogenchloride; In water; pH=2 - 3;

Reference yield: 84.0%

benzyl chloroformate (501-53-1,94274-21-2) + (R)-nipecotic acid (498-95-3,25137-00-2,59045-82-8,60252-41-7,262853-93-0) → (R)-1-((benzyloxy)carbonyl)piperidine-3-carboxylic acid (160706-62-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water;

DOI:10.1039/C9OB00122K

upstream raw materials:

benzyl chloroformate

(R)-nipecotic acid

N-(Benzyloxycarbonyloxy)succinimide

(R)-3-piperidinecarboxylic acid ethyl ester (+)-tartrate

Downstream raw materials:

(R)-3-(tert-butoxycarbonylamino)piperidine-1-carboxylic acid benzyl ester

C₁₄H₁₈N₂O₃

(R)-benzyl 3-aminopiperidine-1-carboxylate

(R)-piperidin-3-ylcarbamic acid tert-butyl ester

Refernces

• 1、 -. "PIPECOLIC ESTERS FOR INHIBITION OF THE PROTEASOME". Paragraph 00274; 00285. . Retrieved 2019/08/26.
• 2、 Al-Horani, Rami A.,Mehta, Akul Y.,Desai, Umesh R.. "Potent direct inhibitors of factor Xa based on the tetrahydroisoquinoline scaffold". experimental part. p. 771 - 783. Retrieved 2012/09/08.