178678-16-5

Basic information

• Product Name: (S)-N-[2-(2,3-Dihydro-6-methoxy-1H-inden-1-yl)ethyl]propanamide
• Synonyms: (S)-N-[2-(2,3-Dihydro-6-methoxy-1H-inden-1-yl)ethyl]propanamide;N-[2-[(1S)-2,3-Dihydro-6-Methoxy-1H-inden-1-yl]ethyl]propanaMide
• CAS NO: 178678-16-5
• Molecular Formula: C15H21NO2
• Molecular Weight: 247.33274
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 178678-16-5.mol

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: (S)-N-[2-(2,3-Dihydro-6-methoxy-1H-inden-1-yl)ethyl]propanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-[2-(2,3-Dihydro-6-methoxy-1H-inden-1-yl)ethyl]propanamide(178678-16-5)
• EPA Substance Registry System: (S)-N-[2-(2,3-Dihydro-6-methoxy-1H-inden-1-yl)ethyl]propanamide(178678-16-5)

Safety Data

• Hazardous Substances Data: 178678-16-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Intermediate in the production of Ramelteon.

Upstream product

• 196598-36-4 (Z)-N-[2-(6-methoxyindan-1-ylidene)-ethyl]propionamide 
• 196597-82-7 (Z)-N-[2-(6-methoxyindan-1-ylidene)ethyl]propionamide 
• 1272319-71-7 C₂₃H₂₅NO₄ 
• 1272319-72-8 C₁₃H₁₈O₂ 
• 1272319-73-9 C₁₅H₂₀O₃ 
• 1272319-74-0 C₁₄H₁₈O₅ 
• 1272319-75-1 C₁₄H₁₆O₄ 
• 1272319-76-2 (S)-2-(6-methoxy-2,3-dihydro-1H-inden-1-yl)ethanol 
• 1272319-77-3 (S)-2-(2-(6-methoxy-2,3-dihydro-1H-inden-1-yl)ethyl)isoindoline-1,3-dione 
• 6099-04-3 3-methoxycinnamic acid 
• 123-62-6 propionic acid anhydride 
• 468104-16-7 (S)-2-(6-methoxy-2,3-dihydro-1H-inden-1-yl)ethanamine hydrochloride 
• 591-31-1 3-methoxy-benzaldehyde 
• 56030-38-7 3-methoxycinnamoyl chloride 

Downstream Products

• 196597-83-8 (S)-N-[2-(5-bromo-6-methoxy-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide 

Relevant articles and documents

Approach to the stereoselective synthesis of melatonin receptor agonist Ramelteon via asymmetric hydrogenation

Asymmetric synthesis of a novel non-benzodiazepine hypnotic drug Ramelteon (TAK-375) was accomplished via asymmetric hydrogenation. Development of the substrate design revealed that a novel class of substrate, allylic acylamine 4a, was hydrogenated with a Ru-BINAP catalyst in 95% ee and 98% yield. The effectiveness and robustness of the reaction were demonstrated on a 700-g scale.

Stereoselective synthesis of melatonin receptor agonist ramelteon via asymmetric michael addition

Highly enantioselective asymmetric Michael addition was used to synthesize ramelteon and its analogue. The asymmetric strategy provides an efficient approach for the medicinal modification of ramelteon with high ee value.

Synthesis of the key intermediate of ramelteon

Asymmetric conjugated addition of allylcopper reagents derived from an allyl Grignard reagent and CuBr·Me2S to chiral α,β-unsaturated N-acyl oxazolidinones has been achieved. The synthetic procedure was applied to the preparation of the key intermediate of the novel nonbenzodiazepine hypnotic drug, ramelteon.

Bicyclic compounds and pharmaceutical composition containing tricyclic compound for treating or preventing sleep disorders

A compound having the following general fomula: wherein R1 is an optionally substituted hydrocarbon, amino or heterocyclic group; R2 is H or an optionally substituted hydrocarbon group; R3 is H or an optionally substituted hydrocarbon or heterocyclic group; X is CHR4, NR4, O or S in which R4 is H or an optionally substituted hydrocarbon group; R5 is H, a halogen atom, C1-6 alkyl group, a C1-6 alkoxy group, a hydroxy group, a nitro group, a cyano group or an amino group wherein the C1-6 alkyl group, the C1-6 alkoxy group and the amino group may be substituted by 1 to 5 substituents, Y is C or N; ring B is an optionally substituted benzene ring; m = 1 to 4 and n = 0 to 2; L represents a leaving group such as a halogen atom, an alkylsulfonyl group, an alkylsulfonlyoxy group and arylsulfonyloxy group; or a salt thereof.

Synthesis of a novel series of benzocycloalkene derivatives as melatonin receptor agonists

We synthesized a novel series of benzocycloalkene derivatives and evaluated their binding affinities to melatonin receptors. To control the spatial position of the amide group, one of the important pharmacophores, we incorporated an endo double bond, an e

Synthesis of a novel series of tricyclic indan derivatives as melatonin receptor agonists

To develop a new therapeutic agent for sleep disorders, we synthesized a novel series of tricyclic indan derivatives and evaluated them for their binding affinity to melatonin receptors. In our previous paper, we proposed a conformation of the methoxy group favorable for the binding of the MT1 receptor. To fix the methoxy group in an active conformation, we decided to synthesize conformationally restricted tricyclic indan analogues with the oxygen atom in the 6-position incorporated into a furan, 1,3-dioxane, oxazole, pyran, morpholine, or 1,4-dioxane ring system. Among these compounds, indeno[5,4-b]furan analogues were found to be the most potent and selective MT1 receptor ligands and to have superior metabolic stability. The optimization of substituents led to (S)-(-)-22b, which showed very strong affinity for human MT1 (Ki = 0.014 nM), but no significant affinity for hamster MT3 (Ki = 2600 nM) or other neurotransmitter receptors. The pharmacological effects of (S)-(-)-22b were studied in experimental animals, and it was found that a dose of 0.1 mg/kg, po promoted a sleep in freely moving cats, as demonstrated by a decrease in wakefulness and increases in slow wave sleep and rapid eye movement sleep, which lasted for 6 h after administration. Melatonin (1 mg/kg, po) also had a sleep-promoting effect, though it lasted only 2 h. A new chiral method for the synthesis of (S)-(-)-22b starting from 60, which was prepared from 59 employing asymmetric hydrogenation with the (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl-Ru complex, was developed. (S)-(-)-22b (TAK-375) is currently under clinical trial for the treatment of insomnia and circadian rhythm disorders.

Kinetic resolutions of indan derivatives using bacteria

Racemic indan derivatives have been resolved by the hydrolysis of amide bonds using Corynebacterium ammoniagenes IFO12612 to produce (5)-amine and (R)-amides. In the kinetic resolution of 1 (N-[2-(6-methoxyindan-1-yl)ethyl] acetamide), it was possible to run the reaction to 44% conversion on a 10-g scale, obtaining (S)-amine 4 ((S)-2-(6-methoxy-indan-1-yl)ethylamine) at >99% enantiomeric excess (ee) and (R)-1 at 98% ee.

Tricyclic compounds, their production and use

A compound of the formula: STR1 wherein R1 is an optionally substituted hydrocarbon, amino or heterocyclic group; R2 is H or an optionally substituted hydrocarbon group; R3 is H or an optionally substituted hydrocarbon or heterocyclic group; X is CHR4, NR4, O or S in which R4 is H or an optionally substituted hydrocarbon group; Y is C, CH or N; ring A is optionally substituted 5- to 7-membered ring; ring B is an optionally substituted benzene ring; and m is 1 to 4, or a salt thereof, a process for producing it, an intermediate for the production and a pharmaceutical composition comprising it are provided.