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CAS No.: | 78715-23-8 |
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Name: | NORBUPRENORPHINE |
Article Data: | 8 |
Molecular Structure: | |
Formula: | C25H35 N O4 |
Molecular Weight: | 413.557 |
Synonyms: | 6,14-Ethenomorphinan-7-methanol,a-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-a-methyl-, [5a,7a(S)]-; N-De(cyclopropylmethyl)buprenorphine;N-Dealkylbuprenorphine; N-Desalkylbuprenorphine; Norbuprenorphine |
Density: | 1.27g/cm3 |
Melting Point: | 221-224°C |
Boiling Point: | 562.7°C at 760 mmHg |
Flash Point: | 294.1°C |
Hazard Symbols: | F,T |
Risk Codes: | 11-23/24/25-39/23/24/25 |
Safety: | 16-36/37-45-7 |
PSA: | 70.95000 |
LogP: | 3.62020 |
norbuprenorphine
Conditions | Yield |
---|---|
With water; potassium hydroxide In diethylene glycol at 185℃; Product distribution / selectivity; Inert atmosphere; | 97.19% |
With potassium hydroxide In diethylene glycol at 100 - 200℃; for 1h; Inert atmosphere; | 3.2 g |
(S)-2-((4R,4aS,6R,7R,7aR,12bS)-7,9-dimethoxy-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-6-yl)-3,3-dimethylbutan-2-ol
norbuprenorphine
Conditions | Yield |
---|---|
Stage #1: (S)-2-((4R,4aS,6R,7R,7aR,12bS)-7,9-dimethoxy-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-6-yl)-3,3-dimethylbutan-2-ol With water; potassium hydroxide In diethylene glycol at 185℃; for 5.25h; Stage #2: With sulfuric acid In water; diethylene glycol at 90℃; pH=8.6; | 80% |
[5α,7α]-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol
A
(S)-2-((4R,4aS,6R,7R,7aR,12bS)-7,9-dimethoxy-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-6-yl)-3,3-dimethylbutan-2-ol
B
norbuprenorphine
Conditions | Yield |
---|---|
With D-Galactose; Cunninghamella echinulata NRRL 1384 at 28 - 32℃; for 168h; Product distribution / selectivity; Microbiological reaction; Basal fermentation medium; | A 55% B 16.4% |
With Maltose; Cunninghamella echinulata NRRL 1384 at 28 - 32℃; for 168h; Product distribution / selectivity; Microbiological reaction; Basal fermentation medium; | A 47.2% B 13.2% |
With Sucrose; Cunninghamella echinulata NRRL 1384 at 28 - 32℃; for 168h; Product distribution / selectivity; Microbiological reaction; Basal fermentation medium; | A 42.4% B 12.1% |
1-[(5α,7α)-3-methoxy-4,5-epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-17-yl]ethanone
A
[5α,7α]-17-acetyl-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-6-methoxy-α-methyl-6,14-ethenomorphinan-7-methanolamide
B
(S)-2-((4R,4aS,6R,7R,7aR,12bS)-7,9-dimethoxy-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-6-yl)-3,3-dimethylbutan-2-ol
C
norbuprenorphine
Conditions | Yield |
---|---|
With potassium hydroxide In diethylene glycol at 170 - 180℃; for 7h; Inert atmosphere; | A 42% B 10% C 35% |
1-[(5α,7α)-3-methoxy-4,5-epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-17-yl]ethanone
A
[5α,7α]-17-acetyl-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-6-methoxy-α-methyl-6,14-ethenomorphinan-7-methanolamide
B
norbuprenorphine
Conditions | Yield |
---|---|
With potassium hydroxide In diethylene glycol at 170 - 180℃; for 7h; Inert atmosphere; | A 37% B 40% |
norbuprenorphine
Conditions | Yield |
---|---|
With hydrogen; palladium 10% on activated carbon In methanol at 60℃; under 2068.65 Torr; for 2.5h; Product distribution / selectivity; |
1-[(5α,7α)-3-methoxy-4,5-epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-17-yl]ethanone
norbuprenorphine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / diethylene glycol / 7 h / 170 - 180 °C / Inert atmosphere 2: potassium hydroxide / diethylene glycol / 7 h / 170 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide / diethylene glycol / 7 h / 170 - 180 °C / Inert atmosphere 2: potassium hydroxide / diethylene glycol / 7 h / 170 °C View Scheme |
[5α,7α]-17-acetyl-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-6-methoxy-α-methyl-6,14-ethenomorphinan-7-methanolamide
norbuprenorphine
Conditions | Yield |
---|---|
With potassium hydroxide In diethylene glycol at 170℃; for 7h; | |
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.666667h; Reagent/catalyst; Inert atmosphere; |
[5α,7α]-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol
norbuprenorphine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: copper diacetate; palladium diacetate / 1,4-dioxane / 23 h / 80 °C 2: potassium hydroxide / diethylene glycol / 7 h / 170 - 180 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: copper diacetate; palladium diacetate / 1,4-dioxane / 23 h / 80 °C 2: potassium hydroxide / diethylene glycol / 7 h / 170 - 180 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: copper diacetate; palladium diacetate / 1,4-dioxane / 23 h / 80 °C 2: potassium hydroxide / diethylene glycol / 7 h / 170 - 180 °C / Inert atmosphere 3: potassium hydroxide / diethylene glycol / 7 h / 170 °C View Scheme | |
Multi-step reaction with 3 steps 1: copper diacetate; palladium diacetate / 1,4-dioxane / 23 h / 80 °C 2: potassium hydroxide / diethylene glycol / 7 h / 170 - 180 °C / Inert atmosphere 3: potassium hydroxide / diethylene glycol / 7 h / 170 °C View Scheme | |
Multi-step reaction with 2 steps 1: chloroform / 12 h / Reflux 2: potassium hydroxide / diethylene glycol / 1 h / 100 - 200 °C / Inert atmosphere View Scheme |
N-nororipavine
norbuprenorphine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 2: toluene / 80 h / 20 - 80 °C / Inert atmosphere 3: tetrahydrofuran; toluene / 3 h / 50 - 60 °C / Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 21 h / 20 - 70 °C / Inert atmosphere 5: hydrogen; palladium 10% on activated carbon; acetic acid / isopropyl alcohol; water; methanol / 144 h / 60 °C / 760.05 Torr View Scheme |