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(R)-5-Hydroxymethyl tolterodine
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Name

(R)-5-Hydroxymethyl tolterodine

 EINECS N/A
CAS No. 207679-81-0 Density 1.061 g/cm3
PSA 43.70000 LogP 4.52530
Solubility N/A Melting Point 68-72 °C
Formula C22H31NO2 Boiling Point 490.721 °C at 760 mmHg
Molecular Weight 341.494 Flash Point 233.165 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 207679-81-0 (3-[(1R)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxybenzenemethanol) Hazard Symbols N/A
Synonyms

PNU 200577;Benzenemethanol,3-[(1R)-3-[bis(1-methylethyl)- amino]-1-phenylpropyl]-4-hydroxy-;3-[(1R)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxybenzenemethanol;

Article Data 34

(R)-5-Hydroxymethyl tolterodine Synthetic route

(R)-2-[3-(N,N-diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol (R)-(-)-O-acetylmandelic acid salt

207679-81-0

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

Conditions
ConditionsYield
With potassium carbonate In water; toluene at 50℃; for 6h;85%
With potassium carbonate In water; toluene at 50℃; for 6h; Inert atmosphere;85%
With potassium carbonate In water; toluene at 50℃; for 1h;81%

(R)-(-)-3-(3-diisopropylamino-1-phenylpropyl)-4-hydroxybenzoic acid methyl ester

207679-81-0

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

Conditions
ConditionsYield
Stage #1: (R)-(-)-3-(3-diisopropylamino-1-phenylpropyl)-4-hydroxybenzoic acid methyl ester With sodium hydroxide In methanol at 0 - 35℃; Inert atmosphere;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 5 - 25℃; for 4h;
Stage #3: With water; sodium hydroxide In tetrahydrofuran at 0 - 5℃; for 3h;		98%
Stage #1: (R)-(-)-3-(3-diisopropylamino-1-phenylpropyl)-4-hydroxybenzoic acid methyl ester With sodium hydroxide In methanol at 0 - 35℃; Inert atmosphere;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 5 - 25℃;
Stage #3: With water; sodium hydroxide In tetrahydrofuran for 3h;		98%
Stage #1: (R)-(-)-3-(3-diisopropylamino-1-phenylpropyl)-4-hydroxybenzoic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3.5h;
Stage #2: With ammonium chloride In tetrahydrofuran at -10℃;		95%
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran at 0 - 5℃; for 2h; Inert atmosphere;
156755-37-2

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

207679-81-0

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

Conditions
ConditionsYield
With hydrogen; 5% Pd(II)/C(eggshell) In methanol at 50 - 55℃;98%
With hydrogen; nickel In methanol at 20℃; for 4 - 5h;96.5%
With hydrogen In methanol under 3000.3 - 3750.38 Torr;72.5%
1294517-15-9

methyl (R)-(-)-3-(3-diisopropylamino-1-phenyl-propyl)-4-hydroxy-benzoate 2,3-dibenzoyl-D-tartaric acid salt

207679-81-0

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

Conditions
ConditionsYield
Stage #1: methyl (R)-(-)-3-(3-diisopropylamino-1-phenyl-propyl)-4-hydroxy-benzoate 2,3-dibenzoyl-D-tartaric acid salt With sodium hydrogencarbonate In ethyl acetate Inert atmosphere;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3.5h;
Stage #3: With ammonium chloride In tetrahydrofuran at -10 - 20℃; for 0.5h;		95%
Multi-step reaction with 2 steps
1.1: sodium hydrogencarbonate / ethyl acetate; water / Inert atmosphere
2.1: sodium hydroxide / methanol / 0 - 35 °C / Inert atmosphere
2.2: 5 - 25 °C
2.3: 3 h
View Scheme

fesoterodine fumarate

207679-81-0

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 20℃; for 18h;55%
1449220-60-3

D-(+)-menthyl 3-(3-N,N'-diisopropylamino-1(R)-phenyl-propyl)-4-hydroxy-benzoate hydrochloride

207679-81-0

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

Conditions
ConditionsYield
Stage #1: D-(+)-menthyl 3-(3-N,N'-diisopropylamino-1(R)-phenyl-propyl)-4-hydroxy-benzoate hydrochloride With water; sodium hydroxide In dichloromethane pH=7 - 8;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃;		83%
Stage #1: D-(+)-menthyl 3-(3-N,N'-diisopropylamino-1(R)-phenyl-propyl)-4-hydroxy-benzoate hydrochloride With sodium hydroxide In dichloromethane; water pH=7 - 8;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃;		83%
960373-33-5

(R)-6-hydroxymethyl-4-phenylchroman-2-(R)-ol

108-18-9

diisopropylamine

207679-81-0

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

Conditions
ConditionsYield
Stage #1: (R)-6-hydroxymethyl-4-phenylchroman-2-(R)-ol; diisopropylamine With hydrogen; palladium on activated charcoal In methanol at 20℃; under 3000.3 Torr; for 18h;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran
Stage #3: With water In tetrahydrofuran
1333234-72-2

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol (R)-2-acetoxy(phenyl)acetate

207679-81-0

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

Conditions
ConditionsYield
With potassium carbonate In toluene at 50℃; for 2h;70%

(R)-[4-benzyloxy-3-(3-diisopropylamino-1-phenyl-propyl)-phenyl]-methanol fumarate

207679-81-0

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

Conditions
ConditionsYield
Stage #1: (R)-[4-benzyloxy-3-(3-diisopropylamino-1-phenyl-propyl)-phenyl]-methanol fumarate With sodium carbonate; sodium hydroxide In dichloromethane; water
Stage #2: With hydrogen; Raney nickel In methanol		59%
200801-70-3

RS-N,N-diisopropyl-3-(2-hydroxy-5-(hydroxymethyl)phenyl)-3-phenylpropylamine

207679-81-0

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

Conditions
ConditionsYield
Stage #1: RS-N,N-diisopropyl-3-(2-hydroxy-5-(hydroxymethyl)phenyl)-3-phenylpropylamine With D-Malic acid In di-isopropyl ether; isopropyl alcohol at 20 - 80℃;
Stage #2: With sodium hydrogencarbonate In water pH=10; Product distribution / selectivity;		40.2%
Multi-step reaction with 2 steps
1: tert-Amyl alcohol / 25 - 70 °C
2: potassium carbonate / toluene; water / 1 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: tetrahydrofuran / 10 - 55 °C
2: potassium carbonate / toluene; water / 50 - 55 °C
View Scheme

(R)-5-Hydroxymethyl tolterodine Chemical Properties

Molecular Structure of (R)-5-Hydroxymethyl tolterodine (CAS NO.207679-81-0):

Systematic Name: 2-[(1R)-3-(Dipropan-2-ylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol
SMILES: Oc1ccc(cc1[C@@H](c2ccccc2)CCN(C(C)C)C(C)C)CO
InChI: InChI=1/C22H31NO2/c1-16(2)23(17(3)4)13-12-20(19-8-6-5-7-9-19)21-14-18(15-24)10-11-22(21)25/h5-11,14,16-17,20,24-25H,12-13,15H2,1-4H3/t20-/m1/s1
InChIKey: DUXZAXCGJSBGDW-HXUWFJFHBB
Molecular Formula: C22H31NO2
Molecular Weight: 341.49
Index of Refraction: 1.563
Molar Refractivity: 104.604 cm3
Molar Volume: 321.89 cm3
Surface Tension: 42.998 dyne/cm
Density: 1.061 g/cm3
Flash Point: 233.165 °C
Enthalpy of Vaporization: 79.759 kJ/mol
Boiling Point: 490.721 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25 °C

(R)-5-Hydroxymethyl tolterodine Specification

 (R)-5-Hydroxymethyl tolterodine (CAS NO.207679-81-0), its Synonyms are 3-[(1R)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxybenzenemethanol ; Benzenemethanol,3-[(1R)-3-[bis(1-methylethyl)- amino]-1-phenylpropyl]-4-hydroxy- .

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