tert-butyl (R)-2-benzoylpiperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (R)-2-benzoylpiperidine-1-carboxylate
• CAS No.: 203056-16-0
• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.375
• DSSTox Substance ID: DTXSID101199255
• Mol file: 203056-16-0.mol

Synonyms:tert-butyl (R)-2-benzoylpiperidine-1-carboxylate;203056-16-0;Tert-butyl (2R)-2-benzoylpiperidine-1-carboxylate;SCHEMBL2136252;DTXSID101199255;1,1-Dimethylethyl (2R)-2-benzoyl-1-piperidinecarboxylate

Chemical Property of tert-butyl (R)-2-benzoylpiperidine-1-carboxylate

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 289.16779360
• Heavy Atom Count: 21
• Complexity: 380

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCCC1C(=O)C2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCCC[C@@H]1C(=O)C2=CC=CC=C2

Technology Process of tert-butyl (R)-2-benzoylpiperidine-1-carboxylate

There total 8 articles about tert-butyl (R)-2-benzoylpiperidine-1-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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-piperidin-2-yl-phenylmethanone → (R)-N-(tert-butyloxycarbonyl)piperidin-2-yl-phenylmethanone (203056-16-0)

Guidance literature:

(R)-piperidin-2-yl-phenylmethanone; With sodium hydroxide; In 1,4-dioxane; water;

di-tert-butyl dicarbonate; In 1,4-dioxane; water; at 0 - 10 ℃; for 2.5h;

DOI:10.1080/00397911.2017.1293109

Reference yield: 47.0%

phenyllithium (591-51-5) + tert-butyl (2R)-2-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate (203056-15-9) → (R)-N-(tert-butyloxycarbonyl)piperidin-2-yl-phenylmethanone (203056-16-0)

Guidance literature:

In diethyl ether; hexane; at -23 ℃; for 3h;

DOI:10.1021/jm970620j

Reference yield:

N-BOC-D-pipecolic acid (28697-17-8) → (R)-N-(tert-butyloxycarbonyl)piperidin-2-yl-phenylmethanone (203056-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 16.4 g / 1,1'-carbonyldiimidazole / dimethylformamide / 20 °C

With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide;

DOI:10.1080/00304940709458602

upstream raw materials:

phenyllithium

tert-butyl (2R)-2-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate

N-BOC-D-pipecolic acid

di-tert-butyl dicarbonate

Downstream raw materials:

(R)-1-[N-(tert-butyloxycarbonyl)piperidin-2-yl]-1-phenylethene