Product Name

  • Name

    Ramelteon

  • EINECS 200-835-2
  • CAS No. 196597-26-9
  • Article Data30
  • CAS DataBase
  • Density 1.119 g/cm3
  • Solubility
  • Melting Point 113-115 °C
  • Formula C16H21NO2
  • Boiling Point 455.3 °C at 760 mmHg
  • Molecular Weight 259.348
  • Flash Point 229.2 °C
  • Transport Information
  • Appearance crystalline solid
  • Safety 16-36/37
  • Risk Codes 11-20/21/22-36
  • Molecular Structure Molecular Structure of 196597-26-9 (Ramelteon)
  • Hazard Symbols F,Xn
  • Synonyms Propanamide, N-(2-((8S)-1,6,7,8-tetrahydro-2H-indeno(5,4-b)furan-8-yl)ethyl)-;TAK-375;Rozerem;(S)-N-(2-(1,6,7,8-tetrahydro-2H-indeno-(5,4)furan-8-yl)ethyl)propionamide;(S)-N-[2-(1,6,7,8-Tetrahydro-2H-indeno-[5,4-b]furan-8-yl)ethyl]propionamide(196597-26-9);
  • PSA 38.33000
  • LogP 2.95850

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%

Ramelteon Chemical Properties

Product Name: Ramelteon (CAS NO.196597-26-9)

Molecular Formula: C16H21NO2
Molecular Weight: 259.34g/mol
Mol File: 196597-26-9.mol
Melting Point: 113-1150C
Boiling point: 455.3 °C at 760 mmHg
Flash Point: 229.2 °C
Density: 1.119 g/cm3
Surface Tension: 45.2 dyne/cm
Enthalpy of Vaporization: 71.51 kJ/mol
Vapour Pressure: 1.77E-08 mmHg at 25°C
XLogP3-AA: 2.7
H-Bond Donor: 1
H-Bond Acceptor: 2
Structure Descriptors of Ramelteon (CAS NO.196597-26-9):
  IUPAC Name: N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl]ethyl]propanamide
  Canonical SMILES: CCC(=O)NCCC1CCC2=C1C3=C(C=C2)OCC3
  Isomeric SMILES: CCC(=O)NCC[C@@H]1CCC2=C1C3=C(C=C2)OCC3
  InChI: InChI=1S/C16H21NO2/c1-2-15(18)17-9-7-12-4-3-11-5-6-14-13(16(11)12)8-10-19-14/h5-6,12H,2-4,7-10H2,1H3,(H,17,18)/t12-/m0/s1 
  InChIKey: YLXDSYKOBKBWJQ-LBPRGKRZSA-N
Product Categories: Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals

Ramelteon Specification

 Ramelteon , its CAS NO. is 196597-26-9, the synonyms are (-)-N-(2-(((8S)-1,6,7,8-Tetrahydro-2H-indeno(5,4-b)furan-8-yl)ethyl)propanamide ; (S)-N-(2-(1,6,7,8-tetrahydro-2H-indeno-(5,4)furan-8-yl)ethyl)propionamide ; Propanamide, N-(2-((8S)-1,6,7,8-tetrahydro-2H-indeno(5,4-b)furan-8-yl)ethyl)-  ; Rozerem ; TAK-375 ; UNII-901AS54I69 .

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