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

Base Information

• Chemical Name: (S)-N-[2-[2,3-Dihydro-6-hydroxy-7-(2-hydroxyethyl)-1H-inden-1-yl]ethyl]propanamide
• CAS No.: 196597-88-3
• Molecular Formula: C₁₆H₂₃NO₃
• Molecular Weight: 277.364
• Mol file: 196597-88-3.mol

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

Chemical Property of (S)-N-[2-[2,3-Dihydro-6-hydroxy-7-(2-hydroxyethyl)-1H-inden-1-yl]ethyl]propanamide

Chemical Property:

• Melting Point: 144-146 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 512.4±50.0 °C(Predicted)
• PKA: 10.46±0.40(Predicted)
• Density: 1.154±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

(S)-N-[2-[2,3-Dihydro-6-hydroxy-7-(2-hydroxyethyl)-1H-inden-1-yl]ethyl]propanamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the production of Ramelteon.

Technology Process of (S)-N-[2-[2,3-Dihydro-6-hydroxy-7-(2-hydroxyethyl)-1H-inden-1-yl]ethyl]propanamide

There total 10 articles about (S)-N-[2-[2,3-Dihydro-6-hydroxy-7-(2-hydroxyethyl)-1H-inden-1-yl]ethyl]propanamide 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: 91.0%

(S)-N-[2-(5-bromo-6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide (196597-87-2) → (S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide (196597-88-3)

Guidance literature:

With hydrogen; triethylamine; 10percent Pd/C/H₂O; In ethanol; at 20 ℃;

DOI:10.1021/jm0201159

Reference yield:

(S)-N-[2-(5-bromo-6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide (196597-87-2) + butan-1-ol (71-36-3) → (S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide (196597-88-3)

Guidance literature:

With triethylamine; palladium-carbon;

Reference yield:

6-methoxy-2,3-dihydro-1H-inden-1-one (13623-25-1) → (S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide (196597-88-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / tetrahydrofuran / 20 °C

1.2: tetrahydrofuran / 20 °C

2.1: H₂; ethanolic NH₃ / Raney-Co

3.1: Et₃N / tetrahydrofuran / 0 °C

4.1: 86 percent / NaOAc; Br₂ / 0 °C

5.1: 94 percent / BBr₃ / CH₂Cl₂ / 0.67 h / -20 - 20 °C

6.1: NaH / dimethylformamide / 0 °C

6.2: 96 percent / dimethylformamide / 0 °C

7.1: 80 percent / various solvent(s) / 200 - 205 °C

8.1: O₃ / methanol / -78 °C

8.2: 99 percent / NaBH₄ / methanol / 1 h / -70 - 20 °C

9.1: 91 percent / Et₃N; H₂ / 10percent Pd/C/H₂O / ethanol / 20 °C

With ammonia; hydrogen; bromine; sodium acetate; boron tribromide; sodium hydride; ozone; triethylamine; Raney-Co; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.2: Horner-Emmons reaction / 7.1: Claisen rearrangement;

DOI:10.1021/jm0201159

upstream raw materials:

(S)-N-[2-(5-bromo-6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide

6-methoxy-2,3-dihydro-1H-inden-1-one

(E)-(2,3-dihydro-6-methoxy-1H-inden-1-ylidene)acetonitrile

(E)-2-(2,3-dihydro-6-methoxy-1H-inden-1-ylidene)ethanamine

Downstream raw materials:

ramelteon

Refernces

• 1、 -. "Bicyclic compounds and pharmaceutical composition containing tricyclic compound for treating or preventing sleep disorders". Referential example 35. . Retrieved 2010/11/29.