(6S,6aR,9R,10aR)-9-hydroxy-6-methyl-3-[(5-phenylpentan-2-yl)oxy]-5,6,6a,7,8,9,10,10a-octahydrophenanthridin-1-yl acetate hydrochloride (1:1)

Base Information

• Chemical Name: (6S,6aR,9R,10aR)-9-hydroxy-6-methyl-3-[(5-phenylpentan-2-yl)oxy]-5,6,6a,7,8,9,10,10a-octahydrophenanthridin-1-yl acetate hydrochloride (1:1)
• CAS No.: 77209-75-7
• Molecular Formula: C₂₇H₃₅NO₄*(x)ClH
• Mol file: 77209-75-7.mol

Synonyms:

Chemical Property of (6S,6aR,9R,10aR)-9-hydroxy-6-methyl-3-[(5-phenylpentan-2-yl)oxy]-5,6,6a,7,8,9,10,10a-octahydrophenanthridin-1-yl acetate hydrochloride (1:1)

Chemical Property:

• Vapor Pressure: 7.57E-15mmHg at 25°C
• Boiling Point: 591.7°Cat760mmHg
• Flash Point: 311.7°C
• Density: g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,6aR,9R,10aR)-9-hydroxy-6-methyl-3-[(5-phenylpentan-2-yl)oxy]-5,6,6a,7,8,9,10,10a-octahydrophenanthridin-1-yl acetate hydrochloride (1:1)

There total 18 articles about (6S,6aR,9R,10aR)-9-hydroxy-6-methyl-3-[(5-phenylpentan-2-yl)oxy]-5,6,6a,7,8,9,10,10a-octahydrophenanthridin-1-yl acetate hydrochloride (1:1) 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: 94.0%

levonantradol → (6S,6aR,9R,10aR)-5,6,6a,7,8,9,10,10a-octahydro-1-acetoxy-9-hydroxy-6-methyl-3-[(R)-5-phenyl-2-pentyloxy]benzo[c]quinoline hydrochloride (77209-75-7)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; diethyl ether; at 0 ℃;

DOI:10.1039/c3cc41388h

Reference yield:

(S)-5-hydroxy-2-methyl-7-[(R)-5-phenyl-2-pentyloxy]-2,3-dihydroquinolin-4(1H)-one (1429484-72-9) → (6S,6aR,9R,10aR)-5,6,6a,7,8,9,10,10a-octahydro-1-acetoxy-9-hydroxy-6-methyl-3-[(R)-5-phenyl-2-pentyloxy]benzo[c]quinoline hydrochloride (77209-75-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / toluene; mineral oil / 0.08 h / 20 °C / Inert atmosphere

1.2: 20 h / 20 °C

2.1: triethylamine / dichloromethane / 20 h / 20 °C / Inert atmosphere

2.2: 4 h / 0 °C

3.1: sodium / methanol / 48 h / Reflux; Inert atmosphere

4.1: ammonia; lithium / tetrahydrofuran / 0.33 h / -70 °C / Inert atmosphere

5.1: triethylamine; dmap / dichloromethane / 0 °C / Inert atmosphere

5.2: 1 h / 0 °C / Inert atmosphere

6.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 0.5 h / -70 - -60 °C

7.1: hydrogenchloride / diethyl ether; 1,4-dioxane / 0 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; ammonia; sodium; lithium; sodium hydride; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; toluene; mineral oil;

DOI:10.1039/c3cc41388h

Reference yield:

5-phenyl-2-pentanol phthalate (87025-89-6) → (6S,6aR,9R,10aR)-5,6,6a,7,8,9,10,10a-octahydro-1-acetoxy-9-hydroxy-6-methyl-3-[(R)-5-phenyl-2-pentyloxy]benzo[c]quinoline hydrochloride (77209-75-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: ethyl acetate / 60 °C / Resolution of racemate

2.1: hydrogenchloride; water / diethyl ether / 0.08 h / 20 °C

3.1: water; sodium hydroxide / 0.08 h / Reflux

4.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

5.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 80 - 82 °C / Inert atmosphere

6.1: sodium hydride / toluene; mineral oil / 0.08 h / 20 °C / Inert atmosphere

6.2: 20 h / 20 °C

7.1: triethylamine / dichloromethane / 20 h / 20 °C / Inert atmosphere

7.2: 4 h / 0 °C

8.1: sodium / methanol / 48 h / Reflux; Inert atmosphere

9.1: ammonia; lithium / tetrahydrofuran / 0.33 h / -70 °C / Inert atmosphere

10.1: triethylamine; dmap / dichloromethane / 0 °C / Inert atmosphere

10.2: 1 h / 0 °C / Inert atmosphere

11.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 0.5 h / -70 - -60 °C

12.1: hydrogenchloride / diethyl ether; 1,4-dioxane / 0 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; ammonia; water; sodium; lithium; sodium hydride; potassium carbonate; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1039/c3cc41388h

upstream raw materials:

(S)-5,7-dihydroxy-2-methyl-2,3-dihydroquinolin-4(1H)-one

(S)-5-hydroxy-2-methyl-7-[(R)-5-phenyl-2-pentyloxy]-2,3-dihydroquinolin-4(1H)-one

(2S)-1-formyl-5-hydroxy-2-methyl-4-oxo-3-(3-oxobutyl)-7-[(R)-5-phenyl-2-pentyloxy]-2,3-dihydroquinoline

(6S,6aR)-5,6,6a,7-tetrahydro-1-hydroxy-6-methyl-3-[(R)-5-phenyl-2-pentyloxy]benzo[c]quinoline-9(8H)-one