1185516-79-3

Basic information

• Product Name: (S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile
• Synonyms: (S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile
• CAS NO: 1185516-79-3
• Molecular Formula: C13H13NO
• Molecular Weight: 199.24842
• Mol File: 1185516-79-3.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile(1185516-79-3)
• EPA Substance Registry System: (S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile(1185516-79-3)

Safety Data

• Hazardous Substances Data: 1185516-79-3(Hazardous Substances Data)

Usage

General Description

(S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile is a complex organic compound that is characterized by its tetrahydro-1H-indeno[5,4-b]furan moiety. It is a derivative of acetonitrile, which means it contains a CN group attached to a CH2 group, making it a type of nitrile. The (S) in its name indicates the configuration of the chiral center of this molecule, thus implying it is an enantiomer. As its name suggests, the compound includes the presence of an indene and furan ring, which belong to polycyclic aromatic hydrocarbons. There are not many specifics readily available about the properties or uses for this particular compound, thus it seems to be more relevant for theoretical chemical studies or synthesis.

Upstream product

• 1217272-33-7 1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylacetonitrile 
• 221530-38-7 (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)acetamide 
• 196597-79-2 (E)-2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile 
• 1242672-40-7 C₃₀H₃₅NO₄SSi 
• 221530-44-5 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile 

Downstream Products

• 196597-81-6 (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine 
• 196597-26-9 ramelteon 

Relevant articles and documents

Concise Six-Step Asymmetric Approach to Ramelteon from an Acetophenone Derivative Using Ir, Rh, Cu, and Ni Catalysis

A concise six-step asymmetric synthesis of nearly enantiomerically pure ramelteon was developed from a monocyclic precursor with a 17% overall yield and a 97% ee in the asymmetric step. The synthetically challenging tricyclic 1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan core of ramelteon was assembled by using Ir-catalyzed O-vinylation and Rh-catalyzed vinyl ether annulation through directed C-H bond activation, while the chirality was introduced with enantioselective reduction of an α,β-unsaturated nitrile moiety under hydrosilylation conditions using a CuII/Walphos type catalyst. The presented methodology represents the shortest synthetic approach to ramelteon.

PROCESS FOR THE PREPARATION OF RAMELTEON

A process is described for the preparation on an industrial scale of N-[2-(8S)- 1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl] propionamide, ramelteon, having the structure illustrated below: (I).

PROCESS FOR THE SYNTHESIS OF RAMELTEON AND ITS INTERMEDIATES

The present invention provides processes and intermediates for the synthesis of ramelteon.