538-09-0

Basic information

• Product Name: Nortropine
• Synonyms: 1-alpha-h,5-alpha-h-nortropan-3-alpha-ol;2,3-dihydro-3-hydroxy-nortropidin;3-hydroxy-nortropan;nortropenol;8-AZA-BICYCLO[3.2.1]OCTAN-3-OL;NOR-TROPANOL;NORTROPINE;Nortropin
• CAS NO: 538-09-0
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.18
• EINECS: 1308068-626-2
• Product Categories: pharmacetical;TROSPIUM CHLORIDE;Chiral Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Chiral Reagents, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;API
• Mol File: 538-09-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 108-110°C
• Boiling Point: 229.6 °C
• Flash Point: 116.8 °C
• Appearance: light tan solid
• Density: 1.096
• Refractive Index: 1.52
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly), Water
• PKA: 14.89±0.20(Predicted)
• CAS DataBase Reference: Nortropine(CAS DataBase Reference)
• NIST Chemistry Reference: Nortropine(538-09-0)
• EPA Substance Registry System: Nortropine(538-09-0)

Safety Data

• RTECS: RD0700000
• Hazardous Substances Data: 538-09-0(Hazardous Substances Data)

Usage

Chemical Properties

Light Tan Solid

Uses

Different sources of media describe the Uses of 538-09-0 differently. You can refer to the following data:
1. A metabolite of Atropine
2. A metabolite of Atropine.

InChI:InChI=1/C7H13NO.ClH/c9-7-3-5-1-2-6(4-7)8-5;/h5-9H,1-4H2;1H/t5-,6+,7+;

Synthetic route

3-tropanol (120-29-6) → nortropine (538-09-0)

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)

tropine N-oxide hydrochloride (1234788-77-2) → nortropine (538-09-0) + 3-tropanol (120-29-6)

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%

nortropinone (5632-84-8) → nortropine (538-09-0)

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 (115522-42-4) → nortropine (538-09-0)

Conditions	Yield
With sodium In ammonia	81%

3-tropanol (120-29-6) → (1R,3R,5S)-3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbaldehyde (50626-97-6) + nortropine (538-09-0)

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 (55727-40-7) + sulfuric acid (7664-93-9) → nortropine (538-09-0)

hydrogenchloride (7647-01-0) + 3endo-acetoxy-nortropane-8-carbonitrile → nortropine (538-09-0)

convolamine → nortropine (538-09-0)

Conditions	Yield
With potassium hydroxide

convolvine → nortropine (538-09-0)

hydratropic acid nortropyl ester → nortropine (538-09-0)

Conditions	Yield
With barium dihydroxide

N-acetyl-nortropanol-(3) → nortropine (538-09-0)

Conditions	Yield
With potassium hydroxide

nor-l-hyoscyamine → nortropine (538-09-0)

Conditions	Yield
With barium dihydroxide Hydrolysis;

O-acetyl-N-cyano-nortropine → nortropine (538-09-0)

Conditions	Yield
With hydrogenchloride

1-methyl-4-nitrosobenzene (623-11-0) + 3-tropanol (120-29-6) + potassium hexacyanoferrate(III) → nortropine (538-09-0)

Tropanol (7432-10-2, 911648-75-4) + potassium permanganate → nortropine (538-09-0)

Conditions	Yield
in alkal.Loesung;

tropine-N-oxide → nortropine (538-09-0)

Conditions	Yield
With acetic anhydride Erwaermen einer Loesung des Reaktionsprodukts in wss. Natronlauge;

2-phenyl-propionic acid nortropan-3-yl ester (47004-02-4) + aq. barium hydroxide solution → hydratropic acid (492-37-5, 2328-24-7) + nortropine (538-09-0)

norhyoscyamine (537-29-1) + barium hydroxide → Tropic acid (529-64-6) + nortropine (538-09-0)

Conditions	Yield
Hydrolysis;

8-azabicyclo[3.2.1]octan-3-yl 3,4-dimethoxybenzoate (537-30-4) → nortropine (538-09-0)

Conditions	Yield
With methanol; potassium hydroxide for 3h; Heating;

6-(benzyloxy)-1,3-cycloheptadiene (115522-58-2) → nortropine (538-09-0)

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 (115522-57-1, 150338-86-6) → nortropine (538-09-0)

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 (115522-53-7) → nortropine (538-09-0)

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 (115522-51-5, 115589-51-0) → nortropine (538-09-0)

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 (115522-46-8, 115648-14-1) → nortropine (538-09-0)

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 (115522-45-7, 115589-50-9) → nortropine (538-09-0)

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

atropine (51-55-8) → nortropine (538-09-0)

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 (143557-91-9) → nortropine (538-09-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 1h;

acetonedicarboxylic acid (542-05-2) → nortropine (538-09-0)

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 (83393-23-1) → nortropine (538-09-0)

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 (24424-99-5) + nortropine (538-09-0) → (1R,3S,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (143557-91-9)

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 (538-09-0) → calcium 1-((3r)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)diazen-1-ium-1,2-diolate

Conditions	Yield
With nitrogen(II) oxide; calcium hydroxide In water at 20℃; under 12929 Torr; for 160h; Green chemistry;	96%

formaldehyd (50-00-0) + nortropine (538-09-0) → 3-tropanol (120-29-6)

Conditions	Yield
With sodium tetrahydroborate	95%
With methanol; nickel Hydrogenation;

acetic anhydride (108-24-7) + nortropine (538-09-0) → (1R,3r,5S)-8-acetyl-8-azabicyclo[3.2.1]octan-3-yl acetate (55727-40-7)

Conditions	Yield
With pyridine; dmap at 20℃; for 21h; Inert atmosphere;	94.4%

nortropine (538-09-0) + 3-[4-(3,3-diethyltriaz-1-enyl)phenoxy]propyloxymethylpolystyrene → 3-[4-(3α-hydroxynortropanylazo)phenoxy]propyloxymethylpolystyrene

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 (13916-99-9) + nortropine (538-09-0) → 4-(3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile (870888-46-3)

Conditions	Yield
With pyridine at 220℃; for 0.0833333h; Microwave irradiation;	92%

2-Iodothiophene (3437-95-4) + carbon monoxide (201230-82-2) + nortropine (538-09-0) → ((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(thiophen-2-yl)methanone

Conditions	Yield
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) + carbon monoxide (201230-82-2) + nortropine (538-09-0) → cyclohex-1-en-1-yl((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

Conditions	Yield
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) + nortropine (538-09-0) → N-β-Fluoroethylnortropine hydrochloride

Conditions	Yield
With hydrogenchloride; dichloromethane; sodium carbonate In acetonitrile for 7.5h; Heating;	87.2%

nortropine (538-09-0) + 4-fluoro-2-(trifluoromethyl)benzonitrile (194853-86-6) → 2-trifluoromethyl-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)benzonitrile

Conditions	Yield
With pyridine at 100℃; for 6h;	85%

Hydroxymethyl resin + nortropine (538-09-0) → C8H14NOPol

Conditions	Yield
With thionyl chloride solid phase reaction;	85%

levofloxacin Q-acid (100986-89-8) + nortropine (538-09-0) → (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	Yield
In dimethyl sulfoxide at 160℃; for 5h;	82.4%

carbon monoxide (201230-82-2) + 4-tert-butyl-1-iodo-1-cyclohexene (96133-27-6) + nortropine (538-09-0) → (4-(tert-butyl)cyclohex-1-en-1-yl)((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone

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 (82419-35-0) + nortropine (538-09-0) → 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	Yield
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 + nortropine (538-09-0) → (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	Yield
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) + carbon monoxide (201230-82-2) + nortropine (538-09-0) → ((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(pyridin-2-yl)methanone

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 (591-50-4) + carbon monoxide (201230-82-2) + nortropine (538-09-0) → 1-((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-2-phenylethane-1,2-dione + ((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(phenyl)methanone (204695-89-6)

Conditions	Yield
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) + nortropine (538-09-0) → N-cinnamyltropine

Conditions	Yield
With potassium carbonate In benzene for 3h; Heating;	65%

carbon monoxide (201230-82-2) + (E)-1-iodo-1-octene (42599-17-7) + nortropine (538-09-0) → (E)-1-((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)non-2-en-1-one

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 (60702-69-4) + nortropine (538-09-0) → 2-chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)benzonitrile

Conditions	Yield
With pyridine at 110℃; for 20h;	63%

2-chloro-4-fluorobenzonitrile (60702-69-4) + nortropine (538-09-0) → 2-chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)benzonitrile (899821-15-9)

Conditions	Yield
With pyridine at 110℃; for 20h;	63%

carbon monoxide (201230-82-2) + (1S,4R)-2-iodo-1,7,7-trimethylbicyclo[2.2.1]hept-2-ene (22885-95-6, 29583-84-4) + nortropine (538-09-0) → ((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	Yield
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) + carbon monoxide (201230-82-2) + nortropine (538-09-0) → ((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(pyridin-3-yl)methanone

Conditions	Yield
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) + nortropine (538-09-0) → N-(4-Biphenylmethyl)-nortropin (102960-87-2)

Conditions	Yield
In benzene for 5h; Heating;	61%

(S)-4-(2-hydroxy-1-phenylethylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid + nortropine (538-09-0) → (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	Yield
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) + 17-iodo-androsta-16-ene (26313-26-8) + nortropine (538-09-0) → ((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	Yield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 750.075 Torr; for 6h; Inert atmosphere;	55%

Upstream product

• 120-29-6 3-tropanol 
• 115522-42-4 (1R,3R,5S)-3-Benzyloxy-8-(toluene-4-sulfonyl)-8-aza-bicyclo[3.2.1]octane 
• 5632-84-8 nortropinone 
• 83393-23-1 N-8-benzyl[3.2.1]8-azabicyclooctan-3-one hydrochloride 
• 542-05-2 acetonedicarboxylic acid 
• 1234788-77-2 tropine-N-oxide hydrochloride 
• 143557-91-9 (1R,3S,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate 
• 51-55-8 atropine 
• 115522-45-7 Acetic acid (1R,4S,6S)-6-benzyloxy-4-(toluene-4-sulfonylamino)-cyclohept-2-enyl ester 
• 115522-46-8 Acetic acid (1S,3S,5R)-3-benzyloxy-5-(toluene-4-sulfonylamino)-cycloheptyl ester 
• 115522-51-5 N-((1R,3S,5S)-3-Benzyloxy-5-hydroxy-cycloheptyl)-4-methyl-benzenesulfonamide 
• 115522-53-7 N-((1R,3S,5R)-3-Benzyloxy-5-chloro-cycloheptyl)-4-methyl-benzenesulfonamide 
• 115522-57-1 1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene 
• 115522-58-2 6-(benzyloxy)-1,3-cycloheptadiene 

Downstream Products

• 120-29-6 3-tropanol 
• 4030-20-0 1-((1R,3r,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)ethan-1-one 
• 204695-89-6 ((1R,3R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)(phenyl)methanone 
• 280-05-7 8-azabicyclo[3.2.1]octane 
• 102960-87-2 N-(4-Biphenylmethyl)-nortropin 
• 143557-91-9 (1R,3S,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate 
• 745734-09-2 3-benzyloxy-8-azabicyclo[3.2.1]octane 
• 797763-50-9 3-(3-methyl-1-phenylbutoxy)-8-azabicyclo[3.2.1]octane 
• 797763-58-7 3-(1-phenylethoxy)-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 
• 797763-49-6 3α-benzhydryloxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid methyl ester 

Relevant articles and documents

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