2,6-Piperidinedione, 3-ethyl-3-(4-pyridinyl)-, (S)-

Base Information

• Chemical Name: 2,6-Piperidinedione, 3-ethyl-3-(4-pyridinyl)-, (S)-
• CAS No.: 121742-47-0
• Molecular Formula: C12H14N2O2
• UNII: 04N5N80JIS
• Nikkaji Number: J449.033I
• Wikidata: Q27247660
• Mol file: 121742-47-0.mol

Synonyms:Rogletimide, (S)-;(-)-(S)-Rogletimide;04N5N80JIS;121742-47-0;UNII-04N5N80JIS;2,6-Piperidinedione, 3-ethyl-3-(4-pyridinyl)-, (S)-;2,6-Piperidinedione, 3-ethyl-3-(4-pyridinyl)-, (3S)-;(S)-Rogletimide;Q27247660

Chemical Property of 2,6-Piperidinedione, 3-ethyl-3-(4-pyridinyl)-, (S)-

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 297

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1(CCC(=O)NC1=O)C2=CC=NC=C2
• Isomeric SMILES: CC[C@]1(CCC(=O)NC1=O)C2=CC=NC=C2

Technology Process of 2,6-Piperidinedione, 3-ethyl-3-(4-pyridinyl)-, (S)-

There total 3 articles about 2,6-Piperidinedione, 3-ethyl-3-(4-pyridinyl)-, (S)- 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: 52.0%

(S)-4-Cyano-2-ethyl-2-pyridin-4-yl-butyric acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (121742-49-2) → S-(-)-pyridoglutethimide (121742-47-0,121840-95-7)

Guidance literature:

With sulfuric acid; acetic acid; for 2.5h; Heating;

Reference yield:

methyl 4-pyridineacetate (29800-89-3) → S-(-)-pyridoglutethimide (121742-47-0,121840-95-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) BuLi / 1.) THF, 5 deg C, 2.) -5 to 20 deg C

2: 1.) KH, 2.) potassium t-butoxide / 1.) THF, -5 to 20 deg C, 2.) t-BuOH, 25 deg C

3: 52 percent / H₂SO₄, AcOH / 2.5 h / Heating

With n-butyllithium; sulfuric acid; potassium tert-butylate; potassium hydride; acetic acid;

Reference yield:

Pyridin-4-yl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (121767-99-5) → S-(-)-pyridoglutethimide (121742-47-0,121840-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) KH, 2.) potassium t-butoxide / 1.) THF, -5 to 20 deg C, 2.) t-BuOH, 25 deg C

2: 52 percent / H₂SO₄, AcOH / 2.5 h / Heating

With sulfuric acid; potassium tert-butylate; potassium hydride; acetic acid;

upstream raw materials:

(S)-4-Cyano-2-ethyl-2-pyridin-4-yl-butyric acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

methyl 4-pyridineacetate

Pyridin-4-yl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester