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Dayang Chem (Hangzhou) Co.,Ltd.

DayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe

Ramelteon Manufacturer/High quality/Best price/In stock

Cas:196597-26-9

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

High quality Ramelteon supplier in China

Cas:196597-26-9

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

We can provide GMP validation service that complies with SFDA, FDA, WHO and EU EMPA.Excellent registration team could help us easlily to register our products in different countries.If you and your customer are interested in some products or need CMO

Ramelteon manufacturer/supplier

Cas:196597-26-9

Min.Order:1 Gram

Negotiable

Type:Manufacturers

inquiry

Hebei yanxi chemical co.,LTD.

Sleeping pills and stability.This product is white or white crystalline powder;Odourless and slightly bitter taste.Almost insoluble in water, soluble in hydrochloric acid.In acid or alkali and heat hydrolysis, oral drug under the action of gastric

N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl]ethyl...

Cas:196597-26-9

Min.Order:10000 Gram

FOB Price: $1300.0

Type:Manufacturers

inquiry

Hangzhou Think Chemical Co. Ltd

Ramelteon CAS No.:196597-26-9 Name: Ramelteon Synonyms: (S)-N-[2-(1,6,7,8-Tetrahydro-2H-indeno-[5,4-b]furan-8-yl)ethyl]propionamide Molecular Structure

High purity Ramelteon CAS No.:196597-26-9

Cas:196597-26-9

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

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Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Factory Supply Ramelteon

Cas:196597-26-9

Min.Order:1

Negotiable

Type:Other

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Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

Factory Price API 99% Ramelteon 196597-26-9 GMP Manufacturer

Cas:196597-26-9

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

inquiry

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Ramelteon

Cas:196597-26-9

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Hubei DiBo chemical co., LTD

Name:Ramelteon The alias:CS-1962;TAK-375;ROZEREM;TAK375;TAK375;;N-[2-[(8S)-1,6,Chemicalbook7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]propanamide; CAS NO:196597-26-9 Molecular formula:C16H21NO2 Molecular weight:259.3434 Product Quality

CAS:196597-26-9/Ramelteon/High purity

Cas:196597-26-9

Min.Order:25 Kilogram

FOB Price: $1.0 / 2.0

Type:Other

inquiry

LIDE PHARMACEUTICALS LIMITED

We are a professional chemicals, APIs and plant extract leading manufacturer in China. We are specialized in chemical synthesis, process development of pharmaceutical intermediates, active pharmaceutical ingredients (APIs), plant extract and rare

Ramelteon

Cas:196597-26-9

Min.Order:1 Gram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.O

TIANFU CHEM---Ramelteon

Cas:196597-26-9

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufactu

Ramelteon CAS 196597-26-9

Cas:196597-26-9

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

Type:Trading Company

inquiry

Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

Factory direct supply CAS 196597-26-9 with best quality

Cas:196597-26-9

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

Ramelteon CAS196597-26-9

Cas:196597-26-9

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

inquiry

Hebei Sankai Chemical Technology Co., Ltd

1. Product advantages High purity, all above 98.5%, no impurities after dissolution We will test each batch to ensure quality OEM and private brand services designed for free Various cap colors available We can also provide MT1 peptide powder 2. Fact

RamelteonCAS196597-26-9

Cas:196597-26-9

Min.Order:1 Kilogram

FOB Price: $9.0 / 10.0

Type:Trading Company

inquiry

Henan Sinotech Import&Export Corporation

Name: Ramelteon Synonyms: N-{2-[(8S)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]fur-8-yl]ethyl}propanamid CAS:196597-26-9 MF: C16H21NO2 Appearance: white powder Storage:Store in cool and dry place, away from sun light. Package: 25kgs/drum Applicatio

Ramelteon

Cas:196597-26-9

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

inquiry

Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

Ramelteon 196597-26-9

Cas:196597-26-9

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At prese

melatonin receptor agonist, Ramelteon CAS:196597-26-9

Cas:196597-26-9

Min.Order:1 Gram

FOB Price: $42.0 / 48.0

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates, steroids, pharmaceutical

Ramelteon/196597-26-9/Ramelteon Manufacturer

Cas:196597-26-9

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Terui OP New Material Technology Co., Ltd.

We generally use secure shipping methods that do not require you to do any customs clearance. Free shipping to your address without worrying about any customs issues. We have a professional customs clearance team to 100% guarantee the safe delivery o

196597-26-9 99% Ramelteon Fast & Safe Shipping Free Customs DDP

Cas:196597-26-9

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

Ramelteon

Cas:196597-26-9

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hubei Jiutian Bio-medical Technology Co., Ltd

1,we produce and sell good chemicals around the world. 2,our success rate is about 95%. this means, if customer order is accepted, the probability that the customer will obtain the ordered substances, is 95%. 3,our staff consists of highly qualifie

CAS 196597-26-9 Ramelteon

Cas:196597-26-9

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

CAS NO.:196597-26-9

Cas:196597-26-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Mojin Biotechnology Co.,Ltd

Hebei Mojin Biotechnology Co., Ltd, Our company is a professional chemical raw materials and chemical reagents research and development production enterprises. We have several production line,So we can control the lowest price. We also have several

Ramelteon cas:196597-26-9

Cas:196597-26-9

Min.Order:25 Gram

FOB Price: $90.0 / 100.0

Type:Trading Company

inquiry

Lonwin Chemical Group Limited

Ramelteon CAS: 196597-26-9 Specification Item Standard Structural data confirmation 1. H-NMR: The data of structure are identical with reference standard 2. HPLC-MS: Ensure the mo

Factory supply Ramelteon

Cas:196597-26-9

Min.Order:1 Kilogram

Negotiable

Type:Other

inquiry

Triumph International Development Limilted

Appearance:white or light yellow crystalline powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:By

ramelteon 196597-26-9

Cas:196597-26-9

Min.Order:100 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Afine Chemicals Limited

Our Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter

Ramelteon

Cas:196597-26-9

Min.Order:1 Kilogram

FOB Price: $1.0 / 100000.0

Type:Lab/Research institutions

inquiry

Hubei Yuanmeng Biological Technology Co., Ltd.

Hubei Yuanmeng Biological Technology Co., Ltd., which is located in Wuhan, China. We are specializing in the exportation of APIs, and plant extracts ect. Our products has been exported to America, Australia, Brazil, the Europe, Middle East and other

High Purity Ramelteon CAS 196597-26-9 with Fast Shipment

Cas:196597-26-9

Min.Order:1 Kilogram

FOB Price: $3.0 / 5.0

Type:Trading Company

inquiry

Taizhou Crene Biotechnology co.ltd

Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-

Ramelteon 196597-26-9

Cas:196597-26-9

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Keyingchem Co.,Ltd

Hangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det

(S)-N-[2-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]- Propionamide (Ramelteon)

Cas:196597-26-9

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine hydrochloride

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine hydrochloride

propionyl chloride
79-03-8

propionyl chloride

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 1h;97.4%
Stage #1: (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine hydrochloride With sodium hydroxide In tetrahydrofuran; water at 15℃;
Stage #2: propionyl chloride In tetrahydrofuran; water at 20℃;
96%
With sodium hydroxide In tetrahydrofuran; water92%
(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine

propionyl chloride
79-03-8

propionyl chloride

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;90%
With sodium hydroxide In tetrahydrofuran at 20℃; for 2h;
With triethylamine In dichloromethane at 20℃; for 2h;n/a
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

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

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

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Stage #1: 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;
Stage #2: With triethylamine In ethyl acetate Heating; Further stages.;
86%
With hydrogenchloride; sodium hydrogencarbonate; triethylamine In pyridine; water; ethyl acetate
(S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide
196597-88-3

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

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Stage #1: (S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide With methanesulfonyl chloride In pyridine at -10 - -5℃; for 0.833333h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate at -10 - 20℃; for 0.5h;
Stage #3: With triethylamine for 0.666667h; Heating / reflux;
86%
(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine dibenzoyl-L-tartaric acid

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine dibenzoyl-L-tartaric acid

propionyl chloride
79-03-8

propionyl chloride

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Stage #1: (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine dibenzoyl-L-tartaric acid With water; sodium hydroxide In tetrahydrofuran at -10℃;
Stage #2: propionyl chloride In tetrahydrofuran at -10 - 20℃; for 2h;
85%
Stage #1: (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine dibenzoyl-L-tartaric acid With sodium hydroxide In dichloromethane; water
Stage #2: propionyl chloride In tetrahydrofuran; water at 20℃; Cooling with ice;
(S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile
1185516-79-3

(S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile

propionic acid anhydride
123-62-6

propionic acid anhydride

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Stage #1: (S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile; propionic acid anhydride With hydrogen; Raney-Ni In tetrahydrofuran at 80℃; under 3000.3 Torr;
Stage #2: With sodium hydroxide In tetrahydrofuran; toluene for 0.5h;
81%
With hydrogen; platinum on carbon In tetrahydrofuran at 65℃; under 7500.75 - 9000.9 Torr; Product distribution / selectivity;
2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethanamine oxalate

2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethanamine oxalate

propionyl chloride
79-03-8

propionyl chloride

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
With sodium carbonate In dichloromethane; water at -5 - 10℃;80%
(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine hydrochloride

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine hydrochloride

propionic acid anhydride
123-62-6

propionic acid anhydride

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
With sodium hydroxide In water at 10 - 60℃; pH=6.0 - 6.5;73%
Stage #1: (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine hydrochloride With sodium hydroxide In tetrahydrofuran; water
Stage #2: propionic acid anhydride In tetrahydrofuran; water at 20 - 25℃;
(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine

propionic acid anhydride
123-62-6

propionic acid anhydride

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h; optical yield given as %ee;62%
2-((S)-2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetaldehyde

2-((S)-2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetaldehyde

Propionamid
79-05-0

Propionamid

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In toluene at 80℃; for 24h;54%
2-(1,6-dihydro-2H-indeno[5,4-b]furan-8-yl)acetamide
221530-40-1

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

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: H2; Ru(OAc)2[(R)-binap] / ethanol / 6 h / 50 °C / 75006 Torr
2.1: BF3*Et2O; NaBH4 / tetrahydrofuran / 24 h / 20 °C
2.2: 63 percent / aq. HCl / ethyl acetate
View Scheme
(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)acetamide
221530-38-7

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)acetamide

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: BF3*Et2O; NaBH4 / tetrahydrofuran / 24 h / 20 °C
1.2: 63 percent / aq. HCl / ethyl acetate
View Scheme
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C
2: triethylamine / dichloromethane / 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 16 - 26 h / -10 - 20 °C
2.1: sodium hydroxide; water / toluene / 0.5 h / 20 °C
2.2: 0.67 h
View Scheme
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one
196597-78-1

1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C
1.2: 83 percent / tetrahydrofuran / 2 h / 20 °C
2.1: 32 percent / aq. H2O2; KOH / dimethylsulfoxide; H2O / 3 h / 20 °C
3.1: H2; Ru(OAc)2[(R)-binap] / ethanol / 6 h / 50 °C / 75006 Torr
4.1: BF3*Et2O; NaBH4 / tetrahydrofuran / 24 h / 20 °C
4.2: 63 percent / aq. HCl / ethyl acetate
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydride / tetrahydrofuran / 1 h / 25 °C / Large scale
1.2: 3.5 h / Large scale
2.1: sodium tetrahydroborate / ethanol / 2 h / Large scale
3.1: hydrogenchloride / water; methanol / 1 h / 45 °C / Large scale
4.1: palladium on activated charcoal; hydrogen / methanol / 1 h / 60 °C / 750.08 Torr / Large scale
5.1: methanol / 1 h / 55 - 60 °C / Large scale
6.1: sodium hydroxide / tetrahydrofuran; water / 0.08 h / Large scale
6.2: 2 h / 10 °C / Large scale
View Scheme
Multi-step reaction with 5 steps
1.1: sodium methylate / 5 - 25 °C
2.1: ammonia / nickel / ethanol / 3 - 4 h / 50 °C / 14711.4 Torr
3.1: isopropyl alcohol / 24 h / 26 °C
4.1: dichloromethane
4.2: 26 °C
5.1: toluene / -5 - 0 °C
5.2: 0.25 - 0.33 h
View Scheme
Multi-step reaction with 9 steps
1.1: sodium hydride / toluene / 2 h / 0 - 5 °C
1.2: 15 - 18 h / 90 - 100 °C
2.1: hydrogen / palladium 10% on activated carbon / methanol; water / 2 - 3 h / 20 °C
3.1: methanol; sodium hydroxide; water / 2 - 3 h / 20 °C
4.1: water; isopropyl alcohol / 0.5 - 0.75 h / 60 - 65 °C / Resolution of racemate
5.1: hydrogenchloride; water / pH 2.0
6.1: triethylamine / dichloromethane / 1 - 2 h / -10 - 0 °C
7.1: ammonia / dichloromethane / 0.5 - 0.75 h / -10 - 0 °C
8.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 16 - 26 h / -10 - 20 °C
9.1: sodium hydroxide; water / toluene / 0.5 h / 20 °C
9.2: 0.67 h
View Scheme
Multi-step reaction with 9 steps
1.1: sodium hydride / toluene / 2 h / 0 - 5 °C
1.2: 15 - 18 h / 90 - 100 °C
2.1: hydrogen / palladium 10% on activated carbon / methanol; water / 2 - 3 h / 20 °C
3.1: methanol; sodium hydroxide; water / 2 - 3 h / 20 °C
4.1: water; isopropyl alcohol / 0.5 - 0.75 h / 60 - 65 °C / Resolution of racemate
5.1: hydrogenchloride; water / pH 2.0
6.1: thionyl chloride / 3 h / 20 °C
7.1: ammonia / dichloromethane; water
8.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 16 - 26 h / -10 - 20 °C
9.1: sodium hydroxide; water / toluene / 0.5 h / 20 °C
9.2: 0.67 h
View Scheme
(E)-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)acetonitrile
196597-79-2

(E)-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)acetonitrile

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 32 percent / aq. H2O2; KOH / dimethylsulfoxide; H2O / 3 h / 20 °C
2.1: H2; Ru(OAc)2[(R)-binap] / ethanol / 6 h / 50 °C / 75006 Torr
3.1: BF3*Et2O; NaBH4 / tetrahydrofuran / 24 h / 20 °C
3.2: 63 percent / aq. HCl / ethyl acetate
View Scheme
6-methoxy-2,3-dihydro-1H-inden-1-one
13623-25-1

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

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 10 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
10.1: pyridine / 0.83 h / -10 - -5 °C
10.2: 86 percent / Et3N / ethyl acetate / Heating
View Scheme
(E)-(2,3-dihydro-6-methoxy-1H-inden-1-ylidene)acetonitrile
187871-98-3

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

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: H2; ethanolic NH3 / Raney-Co
2.1: Et3N / tetrahydrofuran / 0 °C
3.1: 86 percent / NaOAc; Br2 / 0 °C
4.1: 94 percent / BBr3 / CH2Cl2 / 0.67 h / -20 - 20 °C
5.1: NaH / dimethylformamide / 0 °C
5.2: 96 percent / dimethylformamide / 0 °C
6.1: 80 percent / various solvent(s) / 200 - 205 °C
7.1: O3 / methanol / -78 °C
7.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C
8.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C
9.1: pyridine / 0.83 h / -10 - -5 °C
9.2: 86 percent / Et3N / ethyl acetate / Heating
View Scheme
(E)-2-(2,3-dihydro-6-methoxy-1H-inden-1-ylidene)ethanamine
178676-73-8

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

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: Et3N / tetrahydrofuran / 0 °C
2.1: 86 percent / NaOAc; Br2 / 0 °C
3.1: 94 percent / BBr3 / CH2Cl2 / 0.67 h / -20 - 20 °C
4.1: NaH / dimethylformamide / 0 °C
4.2: 96 percent / dimethylformamide / 0 °C
5.1: 80 percent / various solvent(s) / 200 - 205 °C
6.1: O3 / methanol / -78 °C
6.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C
7.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C
8.1: pyridine / 0.83 h / -10 - -5 °C
8.2: 86 percent / Et3N / ethyl acetate / Heating
View Scheme
(Z)-N-[2-(6-methoxyindan-1-ylidene)ethyl]propionamide
196597-82-7

(Z)-N-[2-(6-methoxyindan-1-ylidene)ethyl]propionamide

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 86 percent / NaOAc; Br2 / 0 °C
2.1: 94 percent / BBr3 / CH2Cl2 / 0.67 h / -20 - 20 °C
3.1: NaH / dimethylformamide / 0 °C
3.2: 96 percent / dimethylformamide / 0 °C
4.1: 80 percent / various solvent(s) / 200 - 205 °C
5.1: O3 / methanol / -78 °C
5.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C
6.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C
7.1: pyridine / 0.83 h / -10 - -5 °C
7.2: 86 percent / Et3N / ethyl acetate / Heating
View Scheme
(S)-N-[2-(5-bromo-6-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide
196597-84-9

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

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: NaH / dimethylformamide / 0 °C
1.2: 96 percent / dimethylformamide / 0 °C
2.1: 80 percent / various solvent(s) / 200 - 205 °C
3.1: O3 / methanol / -78 °C
3.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C
4.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C
5.1: pyridine / 0.83 h / -10 - -5 °C
5.2: 86 percent / Et3N / ethyl acetate / Heating
View Scheme
(S)-N-[2-(5-bromo-6-methoxy-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide
196597-83-8

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

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 94 percent / BBr3 / CH2Cl2 / 0.67 h / -20 - 20 °C
2.1: NaH / dimethylformamide / 0 °C
2.2: 96 percent / dimethylformamide / 0 °C
3.1: 80 percent / various solvent(s) / 200 - 205 °C
4.1: O3 / methanol / -78 °C
4.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C
5.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C
6.1: pyridine / 0.83 h / -10 - -5 °C
6.2: 86 percent / Et3N / ethyl acetate / Heating
View Scheme
(S)-N-[2-(6-allyloxy-5-bromo-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide
196597-85-0

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

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 80 percent / various solvent(s) / 200 - 205 °C
2.1: O3 / methanol / -78 °C
2.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C
3.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C
4.1: pyridine / 0.83 h / -10 - -5 °C
4.2: 86 percent / Et3N / ethyl acetate / Heating
View Scheme
(S)-N-[2-(7-allyl-5-bromo-6-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide
196597-86-1

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

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: O3 / methanol / -78 °C
1.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C
2.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C
3.1: pyridine / 0.83 h / -10 - -5 °C
3.2: 86 percent / Et3N / ethyl acetate / Heating
View Scheme
(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-(5-bromo-6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C
2.1: pyridine / 0.83 h / -10 - -5 °C
2.2: 86 percent / Et3N / ethyl acetate / Heating
View Scheme
(S)-2-(1,6,7,8,-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine
1092484-07-5

(S)-2-(1,6,7,8,-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Stage #1: (S)-2-(1,6,7,8,-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine; ethylmagnesium bromide In toluene at -5 - 0℃;
Stage #2: With water; acetic acid In toluene for 0.25 - 0.333333h; Product distribution / selectivity;
0.5C2H2O4*C13H17NO

0.5C2H2O4*C13H17NO

propionyl chloride
79-03-8

propionyl chloride

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
With sodium carbonate In dichloromethane; water at -5 - 20℃;
C13H17NO*(x)ClH

C13H17NO*(x)ClH

propionic acid anhydride
123-62-6

propionic acid anhydride

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Stage #1: C13H17NO*(x)ClH With sodium hydroxide In tetrahydrofuran; water at 20 - 25℃;
Stage #2: propionic acid anhydride In tetrahydrofuran; water at 20 - 25℃; for 1h;
C13H17NO*(x)ClH

C13H17NO*(x)ClH

propionyl chloride
79-03-8

propionyl chloride

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 25℃;
(S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile
1185516-79-3

(S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
With hydrogen; propionic acid anhydride; platinum on activated charcoal In tetrahydrofuran at 60 - 70℃; under 7500.75 - 9000.9 Torr; Product distribution / selectivity;
(E)-3-(2,3-dihydrobenzofuran-4-yl)acrylaldehyde
1361396-60-2

(E)-3-(2,3-dihydrobenzofuran-4-yl)acrylaldehyde

ramelteon
196597-26-9

ramelteon

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine / ethanol / 16 h / 0 °C
2.1: sodium dihydrogenphosphate; sodium chlorite / 2-methyl-but-2-ene; water; tert-butyl alcohol / 3 h / 20 °C
3.1: thionyl chloride / dichloromethane / 2 h / 60 °C
3.2: 16 h / 0 - 20 °C
4.1: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 20 °C
5.1: sodium hydroxide / methanol; water / 2 h / Reflux
5.2: 0.5 h / 160 °C / Inert atmosphere
6.1: thionyl chloride / toluene / 2 h / 60 °C
7.1: ammonia / dichloromethane / 0.17 h
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C
9.1: triethylamine / dichloromethane / 1 h / 20 °C
View Scheme
ramelteon
196597-26-9

ramelteon

(S)-N-(2-[4-bromo-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl)propionamide
1204581-51-0

(S)-N-(2-[4-bromo-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl)propionamide

Conditions
ConditionsYield
With bromine; sodium acetate In methanol for 1.5h; Cooling with ice;93%
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

ramelteon
196597-26-9

ramelteon

N-(2-((S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl)-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propanamide

N-(2-((S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl)-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propanamide

Conditions
ConditionsYield
With pyridine; triisopropylsilyl trifluoromethanesulfonate In hexane at 60℃; for 36h; chemoselective reaction;81%
ramelteon
196597-26-9

ramelteon

(S)-N-(2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethyl)propan-1-amine hydrochloride
1376615-06-3

(S)-N-(2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethyl)propan-1-amine hydrochloride

Conditions
ConditionsYield
Stage #1: ramelteon With borane-THF In tetrahydrofuran at 20℃; for 2h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=7;
56%
Stage #1: ramelteon With borane-THF In tetrahydrofuran at 20℃; for 2h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=7;
56%
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