(R)-Ramelteon

Base Information

• Chemical Name: (R)-Ramelteon
• CAS No.: 196597-27-0
• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 259.348
• UNII: E6PEQ72LZ6
• DSSTox Substance ID: DTXSID701144565
• ChEMBL ID: CHEMBL133775
• Mol file: 196597-27-0.mol

Synonyms:(R)-RAMELTEON;196597-27-0;Ramelteon, (R)-;E6PEQ72LZ6;UNII-E6PEQ72LZ6;(R)-N-(2-(1,6,7,8-Tetrahydro-2H-indeno(5,4-b)furan-8-yl)ethyl)propionamide;N-(2-((8R)-1,6,7,8-Tetrahydro-2H-indeno(5,4-b)furan-8-yl)ethyl)propanamide;N-(2-((8R)-2,6,7,8-Tetrahydro-1H-cyclopenta(E)(1)benzofuran-8-yl)ethyl)propanamide;N-[2-[(8R)-2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl]ethyl]propanamide;PropanaMide, N-[2-[(8R)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]-;N-[2-[(8R)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]propanamide;CHEMBL133775;SCHEMBL1566122;DTXSID701144565;E86903;Z3288556529;(R)-N-(2-(2,6,7,8-TETRAHYDRO-1H-INDENO[5,4-B]FURAN-8-YL)ETHYL)PROPIONAMIDE;PropanaMide,N-[2-[(8R)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]-

Chemical Property of (R)-Ramelteon

Chemical Property:

• Boiling Point: 455.3±24.0 °C(Predicted)
• PKA: 16.37±0.46(Predicted)
• Density: 1.119±0.06 g/cm3(Predicted)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 259.157228913
• Heavy Atom Count: 19
• Complexity: 331

Purity/Quality:

≥95% ^*data from raw suppliers

(R)-Ramelteon ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(=O)NCCC1CCC2=C1C3=C(C=C2)OCC3
• Isomeric SMILES: CCC(=O)NCC[C@H]1CCC2=C1C3=C(C=C2)OCC3
• Uses: (R)-Ramelteon is an enantiomer of Ramelteon (R110051), an Melatonin MT1/MT2 receptor agonist. Ramelteon is also known to exert sedative and hypnotic activities.

Technology Process of (R)-Ramelteon

There total 110 articles about (R)-Ramelteon 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: 97.4%

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine hydrochloride + propionyl chloride (79-03-8) → ramelteon (196597-26-9,196597-27-0,196597-17-8)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 1h;

Reference yield: 90.0%

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine (196597-81-6) + propionyl chloride (79-03-8) → ramelteon (196597-26-9,196597-27-0,196597-17-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield: 86.0%

methanesulfonyl chloride (124-63-0) + (S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide (196597-88-3) → ramelteon (196597-26-9,196597-27-0,196597-17-8)

Guidance literature:

methanesulfonyl chloride; (S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide; With pyridine; at -10 - -5 ℃; for 0.833333h;

With triethylamine; In ethyl acetate; Further stages.; Heating;

DOI:10.1021/jm0201159

upstream raw materials:

methanesulfonyl chloride

(S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide

propionyl chloride

2-(1,6-dihydro-2H-indeno[5,4-b]furan-8-yl)acetamide