Product Name

  • Name

    Nortropine

  • EINECS 238-356-6
  • CAS No. 538-09-0
  • Article Data26
  • CAS DataBase
  • Density 1.096 g/cm3
  • Solubility
  • Melting Point 108-110 °C
  • Formula C7H13NO
  • Boiling Point 266.5 °C at 760 mmHg
  • Molecular Weight 127.186
  • Flash Point 115 °C
  • Transport Information
  • Appearance light tan solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 538-09-0 (Nortropine)
  • Hazard Symbols
  • Synonyms 1aH,5aH-Nortropan-3a-ol (8CI);8-Azabicyclo[3.2.1]octan-3-ol, endo-;Nortropine (6CI,7CI);3a-Nortropanol;N-Demethyltropine;NSC 72850;Nortropenol;Nortropin;Tropigenin;endo-8-Azabicyclo[3.2.1]octan-3-ol;
  • PSA 32.26000
  • LogP 0.59050

Synthetic route

3-tropanol
120-29-6

3-tropanol

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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)
tropine N-oxide hydrochloride
1234788-77-2

tropine N-oxide hydrochloride

A

nortropine
538-09-0

nortropine

B

3-tropanol
120-29-6

3-tropanol

Conditions
ConditionsYield
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%
nortropinone
5632-84-8

nortropinone

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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
115522-42-4

(1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
With sodium In ammonia81%
3-tropanol
120-29-6

3-tropanol

A

(1R,3R,5S)-3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbaldehyde
50626-97-6

(1R,3R,5S)-3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbaldehyde

B

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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
55727-40-7

(1R,3r,5S)-8-acetyl-8-azabicyclo[3.2.1]octan-3-yl acetate

sulfuric acid
7664-93-9

sulfuric acid

nortropine
538-09-0

nortropine

hydrogenchloride
7647-01-0

hydrogenchloride

3endo-acetoxy-nortropane-8-carbonitrile

3endo-acetoxy-nortropane-8-carbonitrile

nortropine
538-09-0

nortropine

convolamine

convolamine

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
With potassium hydroxide
convolvine

convolvine

nortropine
538-09-0

nortropine

hydratropic acid nortropyl ester

hydratropic acid nortropyl ester

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
With barium dihydroxide
N-acetyl-nortropanol-(3)

N-acetyl-nortropanol-(3)

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
With potassium hydroxide
nor-l-hyoscyamine

nor-l-hyoscyamine

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
With barium dihydroxide Hydrolysis;
O-acetyl-N-cyano-nortropine

O-acetyl-N-cyano-nortropine

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
With hydrogenchloride
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

3-tropanol
120-29-6

3-tropanol

potassium hexacyanoferrate(III)

potassium hexacyanoferrate(III)

nortropine
538-09-0

nortropine

potassium permanganate

potassium permanganate

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
in alkal.Loesung;
tropine-N-oxide

tropine-N-oxide

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
With acetic anhydride Erwaermen einer Loesung des Reaktionsprodukts in wss. Natronlauge;
2-phenyl-propionic acid nortropan-3-yl ester
47004-02-4

2-phenyl-propionic acid nortropan-3-yl ester

aq. barium hydroxide solution

aq. barium hydroxide solution

A

hydratropic acid
492-37-5, 2328-24-7

hydratropic acid

B

nortropine
538-09-0

nortropine

norhyoscyamine
537-29-1

norhyoscyamine

barium hydroxide

barium hydroxide

A

Tropic acid
529-64-6

Tropic acid

B

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
Hydrolysis;
8-azabicyclo[3.2.1]octan-3-yl 3,4-dimethoxybenzoate
537-30-4

8-azabicyclo[3.2.1]octan-3-yl 3,4-dimethoxybenzoate

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
With methanol; potassium hydroxide for 3h; Heating;
6-(benzyloxy)-1,3-cycloheptadiene
115522-58-2

6-(benzyloxy)-1,3-cycloheptadiene

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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
115522-57-1, 150338-86-6

1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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
115522-53-7

N-((1R,3S,5R)-3-Benzyloxy-5-chloro-cycloheptyl)-4-methyl-benzenesulfonamide

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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
115522-51-5, 115589-51-0

N-((1R,3S,5S)-3-Benzyloxy-5-hydroxy-cycloheptyl)-4-methyl-benzenesulfonamide

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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
115522-46-8, 115648-14-1

Acetic acid (1S,3S,5R)-3-benzyloxy-5-(toluene-4-sulfonylamino)-cycloheptyl ester

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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
115522-45-7, 115589-50-9

Acetic acid (1R,4S,6S)-6-benzyloxy-4-(toluene-4-sulfonylamino)-cyclohept-2-enyl ester

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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
atropine
51-55-8

atropine

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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
143557-91-9

(1R,3S,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 1h;
acetonedicarboxylic acid
542-05-2

acetonedicarboxylic acid

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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
83393-23-1

8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane hydrochloride

nortropine
538-09-0

nortropine

Conditions
ConditionsYield
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
24424-99-5

di-tert-butyl dicarbonate

nortropine
538-09-0

nortropine

(1R,3S,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
143557-91-9

(1R,3S,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate

Conditions
ConditionsYield
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
538-09-0

nortropine

calcium 1-((3r)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)diazen-1-ium-1,2-diolate

calcium 1-((3r)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)diazen-1-ium-1,2-diolate

Conditions
ConditionsYield
With nitrogen(II) oxide; calcium hydroxide In water at 20℃; under 12929 Torr; for 160h; Green chemistry;96%
formaldehyd
50-00-0

formaldehyd

nortropine
538-09-0

nortropine

3-tropanol
120-29-6

3-tropanol

Conditions
ConditionsYield
With sodium tetrahydroborate95%
With methanol; nickel Hydrogenation;
acetic anhydride
108-24-7

acetic anhydride

nortropine
538-09-0

nortropine

(1R,3r,5S)-8-acetyl-8-azabicyclo[3.2.1]octan-3-yl acetate
55727-40-7

(1R,3r,5S)-8-acetyl-8-azabicyclo[3.2.1]octan-3-yl acetate

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 21h; Inert atmosphere;94.4%
nortropine
538-09-0

nortropine

3-[4-(3,3-diethyltriaz-1-enyl)phenoxy]propyloxymethylpolystyrene

3-[4-(3,3-diethyltriaz-1-enyl)phenoxy]propyloxymethylpolystyrene

3-[4-(3α-hydroxynortropanylazo)phenoxy]propyloxymethylpolystyrene

3-[4-(3α-hydroxynortropanylazo)phenoxy]propyloxymethylpolystyrene

Conditions
ConditionsYield
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
13916-99-9

4-fluoronaphthalene-1-carbonitrile

nortropine
538-09-0

nortropine

4-(3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile
870888-46-3

4-(3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile

Conditions
ConditionsYield
With pyridine at 220℃; for 0.0833333h; Microwave irradiation;92%
2-Iodothiophene
3437-95-4

2-Iodothiophene

carbon monoxide
201230-82-2

carbon monoxide

nortropine
538-09-0

nortropine

((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(thiophen-2-yl)methanone

((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(thiophen-2-yl)methanone

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50 - 70℃; under 750.075 Torr; for 6h; Inert atmosphere;92%
1-iodo-1-cyclohexene
17497-53-9

1-iodo-1-cyclohexene

carbon monoxide
201230-82-2

carbon monoxide

nortropine
538-09-0

nortropine

cyclohex-1-en-1-yl((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

cyclohex-1-en-1-yl((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 1h; Inert atmosphere;89%
2-fluoroethyl bromide
762-49-2

2-fluoroethyl bromide

nortropine
538-09-0

nortropine

N-β-Fluoroethylnortropine hydrochloride

N-β-Fluoroethylnortropine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; dichloromethane; sodium carbonate In acetonitrile for 7.5h; Heating;87.2%
nortropine
538-09-0

nortropine

4-fluoro-2-(trifluoromethyl)benzonitrile
194853-86-6

4-fluoro-2-(trifluoromethyl)benzonitrile

2-trifluoromethyl-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)benzonitrile

2-trifluoromethyl-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)benzonitrile

Conditions
ConditionsYield
With pyridine at 100℃; for 6h;85%
Hydroxymethyl resin

Hydroxymethyl resin

nortropine
538-09-0

nortropine

C8H14NOPol

C8H14NOPol

Conditions
ConditionsYield
With thionyl chloride solid phase reaction;85%
levofloxacin Q-acid
100986-89-8

levofloxacin Q-acid

nortropine
538-09-0

nortropine

(S)-(-)-9-fluoro-3,7-dihydro-10-(3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-3-methyl-7-oxo-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid hydrochloride

(S)-(-)-9-fluoro-3,7-dihydro-10-(3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-3-methyl-7-oxo-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid hydrochloride

Conditions
ConditionsYield
In dimethyl sulfoxide at 160℃; for 5h;82.4%
carbon monoxide
201230-82-2

carbon monoxide

4-tert-butyl-1-iodo-1-cyclohexene
96133-27-6

4-tert-butyl-1-iodo-1-cyclohexene

nortropine
538-09-0

nortropine

(4-(tert-butyl)cyclohex-1-en-1-yl)((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

(4-(tert-butyl)cyclohex-1-en-1-yl)((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

Conditions
ConditionsYield
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
82419-35-0

9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acid

nortropine
538-09-0

nortropine

9-fluoro-3,7-dihydro-10-(3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-3-methyl-7-oxo-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid hydrochloride

9-fluoro-3,7-dihydro-10-(3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-3-methyl-7-oxo-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid hydrochloride

Conditions
ConditionsYield
In dimethyl sulfoxide at 160℃; for 5h;76%
(S)-4-(1-(4-fluorophenyl)-2-methoxyethylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid

(S)-4-(1-(4-fluorophenyl)-2-methoxyethylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid

nortropine
538-09-0

nortropine

(S)-{4-[1-(4-fluorophenyl)-2-methoxyethylamino]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl}(3-hydroxy-8-azabicyclo[3.2.1]octane-8-yl)methanone

(S)-{4-[1-(4-fluorophenyl)-2-methoxyethylamino]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl}(3-hydroxy-8-azabicyclo[3.2.1]octane-8-yl)methanone

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;73.8%
2-iodopyridine
5029-67-4

2-iodopyridine

carbon monoxide
201230-82-2

carbon monoxide

nortropine
538-09-0

nortropine

((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(pyridin-2-yl)methanone

((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(pyridin-2-yl)methanone

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50 - 70℃; under 750.075 Torr; for 2h; Inert atmosphere;73%
iodobenzene
591-50-4

iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

nortropine
538-09-0

nortropine

A

1-((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-2-phenylethane-1,2-dione

1-((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-2-phenylethane-1,2-dione

B

((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(phenyl)methanone
204695-89-6

((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(phenyl)methanone

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; Inert atmosphere;A 30%
B 68%
cinnamyl chloride
2687-12-9

cinnamyl chloride

nortropine
538-09-0

nortropine

N-cinnamyltropine

N-cinnamyltropine

Conditions
ConditionsYield
With potassium carbonate In benzene for 3h; Heating;65%
carbon monoxide
201230-82-2

carbon monoxide

(E)-1-iodo-1-octene
42599-17-7

(E)-1-iodo-1-octene

nortropine
538-09-0

nortropine

(E)-1-((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)non-2-en-1-one

(E)-1-((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)non-2-en-1-one

Conditions
ConditionsYield
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
60702-69-4

2-chloro-4-fluorobenzonitrile

nortropine
538-09-0

nortropine

2-chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)benzonitrile

2-chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)benzonitrile

Conditions
ConditionsYield
With pyridine at 110℃; for 20h;63%
2-chloro-4-fluorobenzonitrile
60702-69-4

2-chloro-4-fluorobenzonitrile

nortropine
538-09-0

nortropine

2-chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)benzonitrile
899821-15-9

2-chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)benzonitrile

Conditions
ConditionsYield
With pyridine at 110℃; for 20h;63%
carbon monoxide
201230-82-2

carbon monoxide

(1S,4R)-2-iodo-1,7,7-trimethylbicyclo[2.2.1]hept-2-ene
22885-95-6, 29583-84-4

(1S,4R)-2-iodo-1,7,7-trimethylbicyclo[2.2.1]hept-2-ene

nortropine
538-09-0

nortropine

((1R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)((1S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)methanone

((1R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)((1S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)methanone

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 1h; Inert atmosphere;63%
3-iodopyridine
1120-90-7

3-iodopyridine

carbon monoxide
201230-82-2

carbon monoxide

nortropine
538-09-0

nortropine

((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(pyridin-3-yl)methanone

((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(pyridin-3-yl)methanone

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50 - 70℃; under 750.075 Torr; for 2h; Inert atmosphere;62%
p-phenylbenzyl bromide
2567-29-5

p-phenylbenzyl bromide

nortropine
538-09-0

nortropine

N-(4-Biphenylmethyl)-nortropin
102960-87-2

N-(4-Biphenylmethyl)-nortropin

Conditions
ConditionsYield
In benzene for 5h; Heating;61%
(S)-4-(2-hydroxy-1-phenylethylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid

(S)-4-(2-hydroxy-1-phenylethylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid

nortropine
538-09-0

nortropine

(S)-(3-hydroxy-8-azabicyclo[3.2.1]octane-8-yl)[4-(2-hydroxy-1-phenylethylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]methanone

(S)-(3-hydroxy-8-azabicyclo[3.2.1]octane-8-yl)[4-(2-hydroxy-1-phenylethylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]methanone

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;55.6%
carbon monoxide
201230-82-2

carbon monoxide

17-iodo-androsta-16-ene
26313-26-8

17-iodo-androsta-16-ene

nortropine
538-09-0

nortropine

((10S,13S)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)((1R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

((10S,13S)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)((1R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 6h; Inert atmosphere;55%

Nortropine Chemical Properties

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 Uses

 Nortropine (CAS NO.538-09-0) can be used as a metabolite of Atropine.

Nortropine Toxicity Data With Reference

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 Specification

 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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