1,1-Dimethylethyl 3-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-1-piperidinecarboxylate

Base Information

• Chemical Name: 1,1-Dimethylethyl 3-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-1-piperidinecarboxylate
• CAS No.: 146667-85-8
• Molecular Formula: C₁₉H₂₉NO₅S
• Molecular Weight: 383.509
• DSSTox Substance ID: DTXSID301128682
• Mol file: 146667-85-8.mol

Synonyms:DTXSID301128682;1,1-Dimethylethyl 3-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-1-piperidinecarboxylate;146667-85-8

Chemical Property of 1,1-Dimethylethyl 3-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-1-piperidinecarboxylate

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 383.17664420
• Heavy Atom Count: 26
• Complexity: 556

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCCC2CCCN(C2)C(=O)OC(C)(C)C

Technology Process of 1,1-Dimethylethyl 3-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-1-piperidinecarboxylate

There total 6 articles about 1,1-Dimethylethyl 3-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-1-piperidinecarboxylate 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: 90.0%

p-toluenesulfonyl chloride (98-59-9) + tert-butyl 3-(2-hydroxyethyl)-1-piperidinecarboxylate (146667-84-7) → tert-butyl 3-(2-<4-tolylsulfonyloxy>ethyl)-1-piperidinecarboxylate (146667-85-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

Reference yield:

3-pyridinylethanol (6293-56-7) → tert-butyl 3-(2-<4-tolylsulfonyloxy>ethyl)-1-piperidinecarboxylate (146667-85-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / triethylamine / CH₂Cl₂ / 5 h / Ambient temperature

2: 99 percent / glacial acetic acid, platinum oxide hydrate, hydrogen / ethanol; H₂O / 20 h / 2068.6 Torr

3: 5percent potassium carbonate / dioxane / 24 h

4: tetrabutylammonium fluoride / tetrahydrofuran / 20 h

5: 90 percent / 4-dimethylaminopyridine, triethylamine / CH₂Cl₂

With dmap; platinum(IV) oxide; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water;

Reference yield:

pyridin-3-yl-acetic acid ethyl ester (39931-77-6) → tert-butyl 3-(2-<4-tolylsulfonyloxy>ethyl)-1-piperidinecarboxylate (146667-85-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 2 h

2: 87 percent / triethylamine / CH₂Cl₂ / 5 h / Ambient temperature

3: 99 percent / glacial acetic acid, platinum oxide hydrate, hydrogen / ethanol; H₂O / 20 h / 2068.6 Torr

4: 5percent potassium carbonate / dioxane / 24 h

5: tetrabutylammonium fluoride / tetrahydrofuran / 20 h

6: 90 percent / 4-dimethylaminopyridine, triethylamine / CH₂Cl₂

With dmap; platinum(IV) oxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; water;

upstream raw materials:

p-toluenesulfonyl chloride

tert-butyl 3-(2-hydroxyethyl)-1-piperidinecarboxylate

3-pyridinylethanol

pyridin-3-yl-acetic acid ethyl ester

Downstream raw materials:

tert-butyl 3-vinyl-1-piperidynecarboxylate

Refernces