Conditions | Yield |
---|---|
With DAP(2+)*2BF4(1-); oxygen In acetonitrile at 20℃; Irradiation; | 87% |
With DAP(2+)*2BF4(1-); oxygen In acetonitrile at 20℃; Product distribution; Irradiation; photochemical N-demethylation of var. tert. amines; | 87% |
With sodium hydroxide; water; potassium hexacyanoferrate(III) |
Conditions | Yield |
---|---|
iron In isopropyl alcohol at 60℃; for 2h; Product distribution / selectivity; | A 84% B 5% |
Stage #1: tropine-N-oxide hydrochloride With ferrocene In chloroform for 24h; Reflux; Stage #2: With sodium hydroxide In chloroform; water | A 74% B 8% |
Conditions | Yield |
---|---|
With hydrogen In methanol at 25 - 30℃; under 7500.75 Torr; for 24h; | 83% |
(1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane
nortropine
Conditions | Yield |
---|---|
With sodium In ammonia | 81% |
3-tropanol
A
(1R,3R,5S)-3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbaldehyde
B
nortropine
Conditions | Yield |
---|---|
With oxygen; lithium perchlorate; 9,10-Dicyanoanthracene In acetonitrile at 20℃; Irradiation; | A 15% B 85 % Spectr. |
With oxygen; 9,10-Dicyanoanthracene In acetonitrile at 20℃; Irradiation; | A 27 % Spectr. B 73 % Spectr. |
(1R,3r,5S)-8-acetyl-8-azabicyclo[3.2.1]octan-3-yl acetate
sulfuric acid
nortropine
nortropine
Conditions | Yield |
---|---|
With potassium hydroxide |
nortropine
nortropine
Conditions | Yield |
---|---|
With barium dihydroxide |
nortropine
Conditions | Yield |
---|---|
With potassium hydroxide |
nortropine
Conditions | Yield |
---|---|
With barium dihydroxide Hydrolysis; |
nortropine
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
in alkal.Loesung; |
nortropine
Conditions | Yield |
---|---|
With acetic anhydride Erwaermen einer Loesung des Reaktionsprodukts in wss. Natronlauge; |
2-phenyl-propionic acid nortropan-3-yl ester
A
hydratropic acid
B
nortropine
Conditions | Yield |
---|---|
Hydrolysis; |
Conditions | Yield |
---|---|
With methanol; potassium hydroxide for 3h; Heating; |
6-(benzyloxy)-1,3-cycloheptadiene
nortropine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 77 percent / LiCl, p-benzoquinone / Pd(OAc)2 (7percent) / acetic acid 2: 64 percent / Pd(PPh3)4 (3percent) / acetonitrile; dimethylsulfoxide / 12 h / 20 °C 3: 95 percent / H2 / RhCl(PPh3)3 / ethanol / 15 h / 20 °C / 4560 Torr 4: 95 percent / NaOH / methanol; H2O 5: 95 percent / EtO2C-N=N-CO2Et, ZnCl2, PBu3 / 3 h / 20 °C 6: 90 percent / K2CO3 / methanol / 1 h / 20 °C 7: 81 percent / Na / NH3 View Scheme |
1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene
nortropine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 64 percent / Pd(PPh3)4 (3percent) / acetonitrile; dimethylsulfoxide / 12 h / 20 °C 2: 95 percent / H2 / RhCl(PPh3)3 / ethanol / 15 h / 20 °C / 4560 Torr 3: 95 percent / NaOH / methanol; H2O 4: 95 percent / EtO2C-N=N-CO2Et, ZnCl2, PBu3 / 3 h / 20 °C 5: 90 percent / K2CO3 / methanol / 1 h / 20 °C 6: 81 percent / Na / NH3 View Scheme |
N-((1R,3S,5R)-3-Benzyloxy-5-chloro-cycloheptyl)-4-methyl-benzenesulfonamide
nortropine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / K2CO3 / methanol / 1 h / 20 °C 2: 81 percent / Na / NH3 View Scheme |
N-((1R,3S,5S)-3-Benzyloxy-5-hydroxy-cycloheptyl)-4-methyl-benzenesulfonamide
nortropine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 95 percent / EtO2C-N=N-CO2Et, ZnCl2, PBu3 / 3 h / 20 °C 2: 90 percent / K2CO3 / methanol / 1 h / 20 °C 3: 81 percent / Na / NH3 View Scheme |
Acetic acid (1S,3S,5R)-3-benzyloxy-5-(toluene-4-sulfonylamino)-cycloheptyl ester
nortropine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / NaOH / methanol; H2O 2: 95 percent / EtO2C-N=N-CO2Et, ZnCl2, PBu3 / 3 h / 20 °C 3: 90 percent / K2CO3 / methanol / 1 h / 20 °C 4: 81 percent / Na / NH3 View Scheme |
Acetic acid (1R,4S,6S)-6-benzyloxy-4-(toluene-4-sulfonylamino)-cyclohept-2-enyl ester
nortropine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 95 percent / H2 / RhCl(PPh3)3 / ethanol / 15 h / 20 °C / 4560 Torr 2: 95 percent / NaOH / methanol; H2O 3: 95 percent / EtO2C-N=N-CO2Et, ZnCl2, PBu3 / 3 h / 20 °C 4: 90 percent / K2CO3 / methanol / 1 h / 20 °C 5: 81 percent / Na / NH3 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous KOH-solution 2: water; potassium hexacyanoferrate(III); NaOH-solution View Scheme |
(1R,3S,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
nortropine
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane for 1h; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride; disodium hydrogenphosphate / 25 - 30 °C 2: hydrogen; 5%-palladium/activated carbon / water; methanol / 16 h 3: hydrogen / methanol / 24 h / 25 - 30 °C / 7500.75 Torr View Scheme |
8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane hydrochloride
nortropine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogen; 5%-palladium/activated carbon / water; methanol / 16 h 2: hydrogen / methanol / 24 h / 25 - 30 °C / 7500.75 Torr View Scheme |
di-tert-butyl dicarbonate
nortropine
(1R,3S,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 12h; | 100% |
In tetrahydrofuran at 20℃; | 97% |
With triethylamine In dichloromethane at 20℃; for 16h; | 97% |
nortropine
Conditions | Yield |
---|---|
With nitrogen(II) oxide; calcium hydroxide In water at 20℃; under 12929 Torr; for 160h; Green chemistry; | 96% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate | 95% |
With methanol; nickel Hydrogenation; |
acetic anhydride
nortropine
(1R,3r,5S)-8-acetyl-8-azabicyclo[3.2.1]octan-3-yl acetate
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 21h; Inert atmosphere; | 94.4% |
nortropine
Conditions | Yield |
---|---|
Stage #1: 3-[4-(3,3-diethyltriaz-1-enyl)phenoxy]propyloxymethylpolystyrene With trifluoroacetic acid In dichloromethane at -10℃; for 0.166667h; Stage #2: nortropine In methanol; dichloromethane at -10 - 20℃; Further stages.; | 94% |
4-fluoronaphthalene-1-carbonitrile
nortropine
4-(3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile
Conditions | Yield |
---|---|
With pyridine at 220℃; for 0.0833333h; Microwave irradiation; | 92% |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50 - 70℃; under 750.075 Torr; for 6h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 1h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With hydrogenchloride; dichloromethane; sodium carbonate In acetonitrile for 7.5h; Heating; | 87.2% |
nortropine
4-fluoro-2-(trifluoromethyl)benzonitrile
Conditions | Yield |
---|---|
With pyridine at 100℃; for 6h; | 85% |
Conditions | Yield |
---|---|
With thionyl chloride solid phase reaction; | 85% |
levofloxacin Q-acid
nortropine
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 160℃; for 5h; | 82.4% |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 1h; Inert atmosphere; | 79% |
9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acid
nortropine
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 160℃; for 5h; | 76% |
nortropine
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; | 73.8% |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50 - 70℃; under 750.075 Torr; for 2h; Inert atmosphere; | 73% |
iodobenzene
carbon monoxide
nortropine
B
((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(phenyl)methanone
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; Inert atmosphere; | A 30% B 68% |
Conditions | Yield |
---|---|
With potassium carbonate In benzene for 3h; Heating; | 65% |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 1h; Inert atmosphere; | 65% |
2-chloro-4-fluorobenzonitrile
nortropine
Conditions | Yield |
---|---|
With pyridine at 110℃; for 20h; | 63% |
2-chloro-4-fluorobenzonitrile
nortropine
2-chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)benzonitrile
Conditions | Yield |
---|---|
With pyridine at 110℃; for 20h; | 63% |
carbon monoxide
(1S,4R)-2-iodo-1,7,7-trimethylbicyclo[2.2.1]hept-2-ene
nortropine
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 1h; Inert atmosphere; | 63% |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50 - 70℃; under 750.075 Torr; for 2h; Inert atmosphere; | 62% |
Conditions | Yield |
---|---|
In benzene for 5h; Heating; | 61% |
nortropine
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; | 55.6% |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 6h; Inert atmosphere; | 55% |
Molecular structure of Nortropine (CAS NO.538-09-0):
Product Name: Nortropine
CAS Registry Number: 538-09-0
IUPAC Name: 8-Azabicyclo[3.2.1]octan-3-ol
Molecular Weight: 127.18422 g/mol
Molecular Formula: C7H13NO
XLogP3-AA: 0.3
H-Bond Donor: 2
H-Bond Acceptor: 2
Melting Point: 108-110 °C
Refractive Index: 1.52
Flash Point: 115 °C
Enthalpy of Vaporization: 58.58 kJ/mol
Boiling Point: 266.5 °C at 760 mmHg
Vapour Pressure: 0.00118 mmHg at 25 °C
Product Categories: pharmacetical; Trospium Chloride; Chiral Reagents; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals
Nortropine (CAS NO.538-09-0) can be used as a metabolite of Atropine.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 180mg/kg (180mg/kg) | Annales de Chimie. Vol. 7, Pg. 537, 1962. | |
mouse | LD50 | intravenous | 41mg/kg (41mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 145, Pg. 97, 1963. | |
mouse | LD50 | oral | 1420mg/kg (1420mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 145, Pg. 97, 1963. | |
rabbit | LD50 | intravenous | > 50mg/kg (50mg/kg) | Annales de Chimie. Vol. 7, Pg. 537, 1962. |
Nortropine (CAS NO.538-09-0) also can be called 1alpha-H,5alpha-H-Nortropan-3alpha-ol ; NSC 72850 ; Nortropane, 3-hydroxy- ; Nortropenol ; Nortropidine, 2,3-dihydro-3-hydroxy- ; Nortropin ; Tropigenin ; Tropigenine ; 1-alpha-H,5-alpha-H-Nortropan-3-alpha-ol ; 1alphaH,5alphaH-Nortropan-3alpha-ol (8CI) ; 8-Azabicyclo(3.2.1)octan-3-ol, endo- (9CI) . It is a light tan solid.
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