Tolterodine tartrate supplier | CasNO.124937-52-6

Name
Tolterodine tartrate
EINECS 620-503-4
CAS No. 124937-52-6
Article Data13
CAS DataBase
Density 1.003 g/cm³
Solubility soluble in water
Melting Point 205-210 °C
Formula C₂₂H₃₁NO^.C₄H₆O₆
Boiling Point 442.2 °C at 760 mmHg
Molecular Weight 475.582
Flash Point 192.1 °C
Transport Information
Appearance white-to-off-white crystalline powder
Safety 36/37
Risk Codes 20/21/22
Molecular Structure
Hazard Symbols Xi
Synonyms Phenol, 2-(3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-methyl-, (R)-, (R-(R*,R*))-2,3-dihydroxybutanedioate (1:1) (salt);Detrol (TN);Phenol, 2-((1R)-3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-methyl-, (2R,3R)-2,3-dihydroxybutanedioate (1:1) (salt);(2R,3R)-2,3-dihydroxybutanedioic acid; 2-[(1R)-3-(dipropan-2-ylamino)-1-phenyl-propyl]-4-methyl-phenol;Detrusitol (TN);Detrol;Tolterodine tartrate (JAN/USAN);Detrusitol;Tolterodine tartrate [USAN];Detrol LA;L-(+)- Tolterodine Tartrate;Tolterodine L-Tartrate;Tolterodine-L-Tartrate;(+)-R)-2-{A-[2-(Diisopropylamino)Ethyl]Benzyl}-P-Cresol Tartrate;
PSA 138.53000
LogP 3.21880

Synthetic route

: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Stage #1: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride With sodium carbonate; sodium hydroxide In dichloromethane; water at 20℃; for 1h; Stage #2: L-Tartaric acid In methanol; acetone for 1h; Reflux;	88%
Stage #1: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride With sodium carbonate; sodium hydroxide In dichloromethane; water at 0 - 20℃; for 1h; Stage #2: L-Tartaric acid In methanol; acetone at 0℃; for 2h; Reflux;	30%
Stage #1: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride With sodium hydroxide In dichloromethane; water at 25 - 35℃; for 0.0833333 - 0.166667h; Stage #2: L-Tartaric acid In methanol; dichloromethane; water; acetonitrile at 0 - 35℃; for 6.58333 - 13h; Heating / reflux;
Stage #1: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride With sodium carbonate; sodium hydroxide In dichloromethane; water Stage #2: L-Tartaric acid In ethanol at 0 - 70℃;	n/a

: 837376-36-0
3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Stage #1: 3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide With sodium hydroxide In dichloromethane; water Stage #2: L-Tartaric acid In ethanol at 60 - 85℃;	39%

: 897314-72-6
(+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Stage #1: (+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 5 - 40℃; for 6h; Cooling with ice; Stage #2: L-Tartaric acid In ethanol at 0 - 70℃; Reflux;	37%

N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine: N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
In ethanol at 60 - 85℃;	18%
In ethanol at 0 - 80℃; for 5h; Resolution of racemate;
In methanol; acetone; toluene at 20 - 60℃; for 12.5h; Resolution of racemate;	n/a
In ethanol Product distribution / selectivity;

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Stage #1: tolterodine hydrobromide With potassium hydroxide In water; ethyl acetate for 0.25 - 0.5h; Stage #2: L-Tartaric acid In ethanol; ethyl acetate at 0℃; for 5 - 17h; Product distribution / selectivity;

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
In ethanol at 25 - 30℃; for 0.5h; Product distribution / selectivity; Resolution of racemate;

: 897314-72-6
(+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide

: 87-69-4
L-Tartaric acid

A: 873551-03-2
(S)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate

B: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Stage #1: (+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 70℃; for 6.08333h; Inert atmosphere; Cooling with ice; Stage #2: With sodium hydroxide In acetone; toluene at 40 - 60℃; for 0.25h; Stage #3: L-Tartaric acid In methanol at 0℃; Product distribution / selectivity; Reflux;	A n/a B n/a
Stage #1: (+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 5 - 40℃; for 6h; Cooling with ice; Stage #2: L-Tartaric acid In isopropyl alcohol at 20 - 75℃; for 3.5h; Product distribution / selectivity;	A n/a B n/a

...Expand

: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride

: 87-69-4
L-Tartaric acid

A: 873551-03-2
(S)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate

B: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
In ethanol at 0 - 70℃;	A n/a B n/a

...Expand

: 1043911-42-7
N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propylamine L-tartrate

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
In water; isopropyl alcohol at 20 - 65℃; Purification / work up; Resolution of racemate; Reflux;	n/a

: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-2-propenamide

A: 873551-03-2
(S)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate

B: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen / 5%-palladium/activated carbon / water; 2-methyltetrahydrofuran / 2.5 h / 55 °C / 750.08 Torr 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 6 h / 5 - 40 °C / Cooling with ice 2.2: 3.5 h / 20 - 75 °C View Scheme
Multi-step reaction with 3 steps 1.1: hydrogen / 5%-palladium/activated carbon / water; 2-methyltetrahydrofuran / 2.5 h / 55 °C / 750.08 Torr 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 6 h / 5 - 40 °C / Cooling with ice 2.2: 20 - 60 °C 3.1: ethanol / 0 - 70 °C View Scheme

: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-2-propenamide

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen / 5%-palladium/activated carbon / water; 2-methyltetrahydrofuran / 2.5 h / 55 °C / 750.08 Torr 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 6 h / 5 - 40 °C / Cooling with ice 2.2: 0 - 70 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: hydrogen / 5%-palladium/activated carbon / water; 2-methyltetrahydrofuran / 2.5 h / 55 °C / 750.08 Torr 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 6 h / 5 - 40 °C / Cooling with ice 2.2: 20 - 60 °C 3.1: sodium hydroxide; sodium carbonate / dichloromethane; water 3.2: 0 - 70 °C View Scheme

: 897314-72-6
(+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide

A: 873551-03-2
(S)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate

B: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 6 h / 5 - 40 °C / Cooling with ice 1.2: 20 - 60 °C 2.1: ethanol / 0 - 70 °C View Scheme

: C23H24O4S

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / water / 2 h / 0 °C 2.1: acetonitrile / 12 h / Reflux 3.1: sodium hydroxide / methanol; water / 4 h / Reflux 3.2: 1 h / 20 °C 4.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 20 °C 4.2: 1 h / Reflux View Scheme

: 4850-49-1
1-phenyl-1,3-propanediol

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: iron(III) chloride hexahydrate / dichloromethane / 24 h / Reflux 2.1: sodium hydroxide / dichloromethane; water / 1 h / 40 °C 3.1: triethylamine / water / 2 h / 0 °C 4.1: acetonitrile / 12 h / Reflux 5.1: sodium hydroxide / methanol; water / 4 h / Reflux 5.2: 1 h / 20 °C 6.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 20 °C 6.2: 1 h / Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1.1: iron(III) chloride hexahydrate / dichloromethane / 24 h / Reflux
2.1: sodium hydroxide / dichloromethane; water / 1 h / 40 °C
3.1: triethylamine / water / 2 h / 0 °C
4.1: acetonitrile / 12 h / Reflux
5.1: sodium hydroxide / methanol; water / 4 h / Reflux
5.2: 1 h / 20 °C
6.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 20 °C
6.2: 1 h / Reflux
View Scheme

: 851789-43-0
3-phenyl-3-(2'-hydroxy-5'-methyl)phenylpropanol-1

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / dichloromethane; water / 1 h / 40 °C 2.1: triethylamine / water / 2 h / 0 °C 3.1: acetonitrile / 12 h / Reflux 4.1: sodium hydroxide / methanol; water / 4 h / Reflux 4.2: 1 h / 20 °C 5.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 20 °C 5.2: 1 h / Reflux View Scheme

: 2-(3-(4-nitrobenzenesulfonyloxy)-1-phenylpropyl)-4-methylphenyl p-toluenesulfonate

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetonitrile / 12 h / Reflux 2.1: sodium hydroxide / methanol; water / 4 h / Reflux 2.2: 1 h / 20 °C 3.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 20 °C 3.2: 1 h / Reflux View Scheme

: 94-02-0
ethyl 3-oxo-3-phenylpropionate

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2.1: iron(III) chloride hexahydrate / dichloromethane / 24 h / Reflux 3.1: sodium hydroxide / dichloromethane; water / 1 h / 40 °C 4.1: triethylamine / water / 2 h / 0 °C 5.1: acetonitrile / 12 h / Reflux 6.1: sodium hydroxide / methanol; water / 4 h / Reflux 6.2: 1 h / 20 °C 7.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 20 °C 7.2: 1 h / Reflux View Scheme

Yield

Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate / methanol / 1 h / 20 °C
2.1: iron(III) chloride hexahydrate / dichloromethane / 24 h / Reflux
3.1: sodium hydroxide / dichloromethane; water / 1 h / 40 °C
4.1: triethylamine / water / 2 h / 0 °C
5.1: acetonitrile / 12 h / Reflux
6.1: sodium hydroxide / methanol; water / 4 h / Reflux
6.2: 1 h / 20 °C
7.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 20 °C
7.2: 1 h / Reflux
View Scheme

: 92-48-8
6-methylcoumarin

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: (R)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis[bis(3-fluoro-4-trifluoromethylphenyl)phosphine]; chlorobis(ethylene)rhodium(I) dimer; sodium hydrogencarbonate / toluene; water / 36 h / 25 °C / Schlenk technique; Inert atmosphere 2.1: citric acid; diisobutylaluminium hydride / toluene; hexane; water; ethyl acetate / -25 - 20 °C / Inert atmosphere 3.1: formic acid; Cp*IrCl(8-quinolinolate) / tetrahydrofuran / 20 h / 0 - 50 °C / Schlenk technique; Inert atmosphere 3.2: 4 h / 0 - 80 °C View Scheme

Yield

Multi-step reaction with 3 steps
1.1: (R)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis[bis(3-fluoro-4-trifluoromethylphenyl)phosphine]; chlorobis(ethylene)rhodium(I) dimer; sodium hydrogencarbonate / toluene; water / 36 h / 25 °C / Schlenk technique; Inert atmosphere
2.1: citric acid; diisobutylaluminium hydride / toluene; hexane; water; ethyl acetate / -25 - 20 °C / Inert atmosphere
3.1: formic acid; Cp*IrCl(8-quinolinolate) / tetrahydrofuran / 20 h / 0 - 50 °C / Schlenk technique; Inert atmosphere
3.2: 4 h / 0 - 80 °C
View Scheme

: 98-80-6
phenylboronic acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: (R)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis[bis(3-fluoro-4-trifluoromethylphenyl)phosphine]; chlorobis(ethylene)rhodium(I) dimer; sodium hydrogencarbonate / toluene; water / 36 h / 25 °C / Schlenk technique; Inert atmosphere 2.1: citric acid; diisobutylaluminium hydride / toluene; hexane; water; ethyl acetate / -25 - 20 °C / Inert atmosphere 3.1: formic acid; Cp*IrCl(8-quinolinolate) / tetrahydrofuran / 20 h / 0 - 50 °C / Schlenk technique; Inert atmosphere 3.2: 4 h / 0 - 80 °C View Scheme

Yield

: 827007-19-2
(R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: citric acid; diisobutylaluminium hydride / toluene; hexane; water; ethyl acetate / -25 - 20 °C / Inert atmosphere 2.1: formic acid; Cp*IrCl(8-quinolinolate) / tetrahydrofuran / 20 h / 0 - 50 °C / Schlenk technique; Inert atmosphere 2.2: 4 h / 0 - 80 °C View Scheme

: 828933-86-4
(4R)-6-methyl-4-phenylchroman-2-ol

: 87-69-4
L-Tartaric acid

: 108-18-9
diisopropylamine

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Stage #1: (4R)-6-methyl-4-phenylchroman-2-ol; diisopropylamine With formic acid; Cp*IrCl(8-quinolinolate) In tetrahydrofuran at 0 - 50℃; for 20h; Schlenk technique; Inert atmosphere; Stage #2: L-Tartaric acid In ethanol at 0 - 80℃; for 4h;	940.7 mg

...Expand

: 854306-68-6
3-(2-benzyloxy-5-methylphenyl)-3-phenylpropanol

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: triethylamine; dmap / dichloromethane / 2 h / 20 °C 2.1: acetonitrile / 16 h / Reflux 3.1: hydrogen; palladium on activated charcoal / methanol / 19 h 4.1: hydrogenchloride / methanol / 0.5 h / 0 °C 5.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 0 - 20 °C 5.2: 2 h / 0 °C / Reflux View Scheme

: C29H27NO6S

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetonitrile / 16 h / Reflux 2.1: hydrogen; palladium on activated charcoal / methanol / 19 h 3.1: hydrogenchloride / methanol / 0.5 h / 0 °C 4.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 0 - 20 °C 4.2: 2 h / 0 °C / Reflux View Scheme

: 389068-22-8
N,N-diisopropyl-3-(2-benzyloxy-5-methylphenyl)-3-phenylpropylamine

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen; palladium on activated charcoal / methanol / 19 h 2.1: hydrogenchloride / methanol / 0.5 h / 0 °C 3.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 0 - 20 °C 3.2: 2 h / 0 °C / Reflux View Scheme

: 124936-74-9
N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / methanol / 0.5 h / 0 °C 2.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 0 - 20 °C 2.2: 2 h / 0 °C / Reflux View Scheme

: 40546-94-9
6-methyl-4-phenyl-3,4-dihydrocoumarin

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: potassium carbonate / acetone / 2 h / Reflux 1.2: 2 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 3.1: triethylamine; dmap / dichloromethane / 2 h / 20 °C 4.1: acetonitrile / 16 h / Reflux 5.1: hydrogen; palladium on activated charcoal / methanol / 19 h 6.1: hydrogenchloride / methanol / 0.5 h / 0 °C 7.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 0 - 20 °C 7.2: 2 h / 0 °C / Reflux View Scheme

Yield

Multi-step reaction with 7 steps
1.1: potassium carbonate / acetone / 2 h / Reflux
1.2: 2 h / Reflux
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C
3.1: triethylamine; dmap / dichloromethane / 2 h / 20 °C
4.1: acetonitrile / 16 h / Reflux
5.1: hydrogen; palladium on activated charcoal / methanol / 19 h
6.1: hydrogenchloride / methanol / 0.5 h / 0 °C
7.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 0 - 20 °C
7.2: 2 h / 0 °C / Reflux
View Scheme

: 854306-67-5
methyl 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionate

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: triethylamine; dmap / dichloromethane / 2 h / 20 °C 3.1: acetonitrile / 16 h / Reflux 4.1: hydrogen; palladium on activated charcoal / methanol / 19 h 5.1: hydrogenchloride / methanol / 0.5 h / 0 °C 6.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 0 - 20 °C 6.2: 2 h / 0 °C / Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C
2.1: triethylamine; dmap / dichloromethane / 2 h / 20 °C
3.1: acetonitrile / 16 h / Reflux
4.1: hydrogen; palladium on activated charcoal / methanol / 19 h
5.1: hydrogenchloride / methanol / 0.5 h / 0 °C
6.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 1 h / 0 - 20 °C
6.2: 2 h / 0 °C / Reflux
View Scheme

: 100-39-0
benzyl bromide

: 124937-52-6
tolterodine tartrate

: 848768-06-9
(R)-3-(2-(benzyloxy)-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

Conditions

Conditions	Yield
Stage #1: tolterodine tartrate With sodium carbonate; sodium hydroxide In dichloromethane; water at 0 - 20℃; for 0.583333h; Stage #2: benzyl bromide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 13h;	100%

: 87-88-7
3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone

: 124937-52-6
tolterodine tartrate

: C22H31NO*C4H6O6*C6H2Cl2O4

Conditions

Conditions	Yield
In acetonitrile at 25℃;

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 124937-52-6
tolterodine tartrate

: tolterodine tartarate

Conditions

Conditions	Yield
In acetonitrile at 25℃;

: 124937-52-6
tolterodine tartrate

: 848768-06-9
(R)-3-(2-(benzyloxy)-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C View Scheme

: 124937-52-6
tolterodine tartrate

: (R)-2-(4-(benzyloxy)-3-(3-(diisopropylamino)-1-phenylpropyl)phenyl)acetonitrile

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C 3: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 0 - 20 °C 4: sodium tetrahydroborate; methanol / 13 h / 0 - 20 °C 5: thionyl chloride / dichloromethane / 2 h / 20 °C 6: N,N-dimethyl-formamide / 15 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 0.58 h / 0 - 20 °C 1.2: 13 h / 20 °C 2.1: ammonium cerium (IV) nitrate / acetonitrile; water / 4 h / 0 - 20 °C 3.1: sodium tetrahydroborate / methanol / 13 h / 0 - 20 °C 4.1: thionyl chloride / dichloromethane / 2 h / 20 °C 5.1: N,N-dimethyl-formamide / 15 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C
2: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C
3: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 0 - 20 °C
4: sodium tetrahydroborate; methanol / 13 h / 0 - 20 °C
5: thionyl chloride / dichloromethane / 2 h / 20 °C
6: N,N-dimethyl-formamide / 15 h / 20 °C
View Scheme

Multi-step reaction with 5 steps
1.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 0.58 h / 0 - 20 °C
1.2: 13 h / 20 °C
2.1: ammonium cerium (IV) nitrate / acetonitrile; water / 4 h / 0 - 20 °C
3.1: sodium tetrahydroborate / methanol / 13 h / 0 - 20 °C
4.1: thionyl chloride / dichloromethane / 2 h / 20 °C
5.1: N,N-dimethyl-formamide / 15 h / 20 °C
View Scheme

: 124937-52-6
tolterodine tartrate

: (R)-benzyl 7-((4-(benzyloxy)-3-(3-(diisopropylamino)-1-phenylpropyl)phenethyl)amino)-7-oxoheptanoate

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C 3.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 0 - 20 °C 4.1: sodium tetrahydroborate; methanol / 13 h / 0 - 20 °C 5.1: thionyl chloride / dichloromethane / 2 h / 20 °C 6.1: N,N-dimethyl-formamide / 15 h / 20 °C 7.1: diisobutylaluminium hydride / toluene / 12 h / -78 °C 7.2: 2.5 h / -78 - 0 °C 8.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 0.58 h / 0 - 20 °C 1.2: 13 h / 20 °C 2.1: ammonium cerium (IV) nitrate / acetonitrile; water / 4 h / 0 - 20 °C 3.1: sodium tetrahydroborate / methanol / 13 h / 0 - 20 °C 4.1: thionyl chloride / dichloromethane / 2 h / 20 °C 5.1: N,N-dimethyl-formamide / 15 h / 20 °C 6.1: diisobutylaluminium hydride / toluene / 12 h / -78 °C 6.2: 2.5 h / -78 - 0 °C 7.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C
3.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 0 - 20 °C
4.1: sodium tetrahydroborate; methanol / 13 h / 0 - 20 °C
5.1: thionyl chloride / dichloromethane / 2 h / 20 °C
6.1: N,N-dimethyl-formamide / 15 h / 20 °C
7.1: diisobutylaluminium hydride / toluene / 12 h / -78 °C
7.2: 2.5 h / -78 - 0 °C
8.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C
View Scheme

Multi-step reaction with 7 steps
1.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 0.58 h / 0 - 20 °C
1.2: 13 h / 20 °C
2.1: ammonium cerium (IV) nitrate / acetonitrile; water / 4 h / 0 - 20 °C
3.1: sodium tetrahydroborate / methanol / 13 h / 0 - 20 °C
4.1: thionyl chloride / dichloromethane / 2 h / 20 °C
5.1: N,N-dimethyl-formamide / 15 h / 20 °C
6.1: diisobutylaluminium hydride / toluene / 12 h / -78 °C
6.2: 2.5 h / -78 - 0 °C
7.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C
View Scheme

: 124937-52-6
tolterodine tartrate

: (R)-7-((3-(3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenethyl)amino)-7-oxoheptanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C 3.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 0 - 20 °C 4.1: sodium tetrahydroborate; methanol / 13 h / 0 - 20 °C 5.1: thionyl chloride / dichloromethane / 2 h / 20 °C 6.1: N,N-dimethyl-formamide / 15 h / 20 °C 7.1: diisobutylaluminium hydride / toluene / 12 h / -78 °C 7.2: 2.5 h / -78 - 0 °C 8.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C 9.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 16 h View Scheme
Multi-step reaction with 8 steps 1.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 0.58 h / 0 - 20 °C 1.2: 13 h / 20 °C 2.1: ammonium cerium (IV) nitrate / acetonitrile; water / 4 h / 0 - 20 °C 3.1: sodium tetrahydroborate / methanol / 13 h / 0 - 20 °C 4.1: thionyl chloride / dichloromethane / 2 h / 20 °C 5.1: N,N-dimethyl-formamide / 15 h / 20 °C 6.1: diisobutylaluminium hydride / toluene / 12 h / -78 °C 6.2: 2.5 h / -78 - 0 °C 7.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C 8.1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol / 16 h View Scheme

Yield

Multi-step reaction with 9 steps
1.1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C
3.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 0 - 20 °C
4.1: sodium tetrahydroborate; methanol / 13 h / 0 - 20 °C
5.1: thionyl chloride / dichloromethane / 2 h / 20 °C
6.1: N,N-dimethyl-formamide / 15 h / 20 °C
7.1: diisobutylaluminium hydride / toluene / 12 h / -78 °C
7.2: 2.5 h / -78 - 0 °C
8.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C
9.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 16 h
View Scheme

Multi-step reaction with 8 steps
1.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 0.58 h / 0 - 20 °C
1.2: 13 h / 20 °C
2.1: ammonium cerium (IV) nitrate / acetonitrile; water / 4 h / 0 - 20 °C
3.1: sodium tetrahydroborate / methanol / 13 h / 0 - 20 °C
4.1: thionyl chloride / dichloromethane / 2 h / 20 °C
5.1: N,N-dimethyl-formamide / 15 h / 20 °C
6.1: diisobutylaluminium hydride / toluene / 12 h / -78 °C
6.2: 2.5 h / -78 - 0 °C
7.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C
8.1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol / 16 h
View Scheme

: 124937-52-6
tolterodine tartrate

: C73H128N3O12P

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C 3.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 0 - 20 °C 4.1: sodium tetrahydroborate; methanol / 13 h / 0 - 20 °C 5.1: thionyl chloride / dichloromethane / 2 h / 20 °C 6.1: N,N-dimethyl-formamide / 15 h / 20 °C 7.1: diisobutylaluminium hydride / toluene / 12 h / -78 °C 7.2: 2.5 h / -78 - 0 °C 8.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C 9.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 16 h 10.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / chloroform; tert-butyl alcohol / 0.08 h View Scheme

Yield

Multi-step reaction with 10 steps
1.1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C
3.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 0 - 20 °C
4.1: sodium tetrahydroborate; methanol / 13 h / 0 - 20 °C
5.1: thionyl chloride / dichloromethane / 2 h / 20 °C
6.1: N,N-dimethyl-formamide / 15 h / 20 °C
7.1: diisobutylaluminium hydride / toluene / 12 h / -78 °C
7.2: 2.5 h / -78 - 0 °C
8.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C
9.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 16 h
10.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / chloroform; tert-butyl alcohol / 0.08 h
View Scheme

: 124937-52-6
tolterodine tartrate

: 124937-51-5
(R)-(+)-tolterodine

Conditions

Conditions	Yield
With sodium carbonate; sodium hydroxide In dichloromethane; water at 0 - 20℃; for 0.583333h;
With sodium hydrogencarbonate In ethyl acetate	6.9 g

: 124937-52-6
tolterodine tartrate

: 214601-54-4
(R)-[4-benzyloxy-3-(3-diisopropylamino-1-phenyl-propyl)-phenyl]-methanal

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C 3: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 0.58 h / 0 - 20 °C 1.2: 13 h / 20 °C 2.1: ammonium cerium (IV) nitrate / acetonitrile; water / 4 h / 0 - 20 °C View Scheme

: 124937-52-6
tolterodine tartrate

: 156755-37-2
{4-(benzyloxy)-3-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]phenyl}methanol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C 3: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 0 - 20 °C 4: sodium tetrahydroborate; methanol / 13 h / 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 0.58 h / 0 - 20 °C 1.2: 13 h / 20 °C 2.1: ammonium cerium (IV) nitrate / acetonitrile; water / 4 h / 0 - 20 °C 3.1: sodium tetrahydroborate / methanol / 13 h / 0 - 20 °C View Scheme

: 124937-52-6
tolterodine tartrate

: C29H36ClNO

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydroxide; sodium carbonate / water; dichloromethane / 0.58 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C 3: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 0 - 20 °C 4: sodium tetrahydroborate; methanol / 13 h / 0 - 20 °C 5: thionyl chloride / dichloromethane / 2 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydroxide; sodium carbonate / dichloromethane; water / 0.58 h / 0 - 20 °C 1.2: 13 h / 20 °C 2.1: ammonium cerium (IV) nitrate / acetonitrile; water / 4 h / 0 - 20 °C 3.1: sodium tetrahydroborate / methanol / 13 h / 0 - 20 °C 4.1: thionyl chloride / dichloromethane / 2 h / 20 °C View Scheme

Tolterodine tartrate Chemical Properties

Molecular Structure of Tolterodine tartrate (CAS NO.124937-52-6):

IUPAC Name: (2R,3R)-2,3-dihydroxybutanedioic acid; 2-[(1S)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol
Empirical Formula: C₂₆H₃₇NO₇
Molecular Weight: 475.5745
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 8
Polar Surface Area: 12.47Å²
Flash Point: 192.1 °C
Enthalpy of Vaporization: 72.66 kJ/mol
Boiling Point: 442.2 °C at 760 mmHg
Vapour Pressure: 1.97E-08 mmHg at 25°C
Melting point: 205-210°C
InChI
InChI=1/C22H31NO.C4H6O6/c1-16(2)23(17(3)4)14-13-20(19-9-7-6-8-10-19)21-15-18(5)11-12-22(21)24;5-1(3(7)8)2(6)4(9)10/h6-12,15-17,20,24H,13-14H2,1-5H3;1-2,5-6H,(H,7,8)(H,9,10)/t20-;1-,2-/m01/s1
Smiles
c1([C@H](c2ccccc2)CCN(C(C)C)C(C)C)c(ccc(c1)C)O.C([C@@H]([C@H](C(=O)O)O)O)(=O)O
Product Categories: Active Pharmaceutical Ingredients; Medicine intermediate;APIs; In treatment of urinary incontinence; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Tolterodine

Tolterodine tartrate Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.

Tolterodine tartrate Standards and Recommendations

oxybutynin (M3 and M1 selective, but more so in the parotid than in the bladder) as tolterodine targets the bladder more than other areas of the body. This means that less drug needs to be given daily (due to efficient targeting of the bladder) and so there are fewer side effects.Tolterodine, although it acts on all types of receptors, has fewer side effects than other antimuscarinics eg. Tolterodine acts on M1, M2, M3, M4 and M5 subtypes of muscarinic receptors whereas modern antimuscarinic treatments for overactive bladder only act on M3 receptors making them more selective.

Tolterodine tartrate Specification

Tolterodine tartrate , with CAS number of 124937-52-6, can be called 2-((1R)-3-(Bis(1-methylethyl)amino)-1-phenylpropyl)-4-methylphenol (2R,3R)-2,3-dihydroxybutanedioate (1:1) (salt) ; 2,3-Dihydroxybutandisäure--2-{(1R)-3-[bis(1-methylethyl)amino]-1-phenylpropyl}-4-methylbenzolol(1:1) ; 2-[(1R)-3-(Diisopropylamino)-1-phenylpropyl]-4-methylphenol 2,3-dihydroxysuccinate (1:1) ; acide 2,3-dihydroxybutanedioïque - 2-{(1R)-3-[bis(1-méthyléthyl)amino]-1-phénylpropyl}-4-méthylphénol (1:1) . Tolterodine tartrate (CAS NO.124937-52-6) is used to treat urinary incontinence.Tolterodine is an antimuscarinic drug.

Product Name

Tolterodine tartrate

Synthetic route

Tolterodine tartrate Chemical Properties

Tolterodine tartrate Safety Profile

Tolterodine tartrate Standards and Recommendations

Tolterodine tartrate Specification

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