Product Name

  • Name

    3-[(1R)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxybenzenemethanol

  • EINECS
  • CAS No. 207679-81-0
  • Article Data34
  • CAS DataBase
  • Density 1.061 g/cm3
  • Solubility
  • 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
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 207679-81-0 (3-[(1R)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxybenzenemethanol)
  • Hazard Symbols
  • 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;
  • PSA 43.70000
  • LogP 4.52530

Synthetic route

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

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

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

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

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

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

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
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%
methyl (R)-(-)-3-(3-diisopropylamino-1-phenyl-propyl)-4-hydroxy-benzoate 2,3-dibenzoyl-D-tartaric acid salt
1294517-15-9

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

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

fesoterodine fumarate

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 20℃; for 18h;55%
D-(+)-menthyl 3-(3-N,N'-diisopropylamino-1(R)-phenyl-propyl)-4-hydroxy-benzoate hydrochloride
1449220-60-3

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

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
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%
(R)-6-hydroxymethyl-4-phenylchroman-2-(R)-ol
960373-33-5

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

diisopropylamine
108-18-9

diisopropylamine

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
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
(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol (R)-2-acetoxy(phenyl)acetate
1333234-72-2

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

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

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

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
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%
RS-N,N-diisopropyl-3-(2-hydroxy-5-(hydroxymethyl)phenyl)-3-phenylpropylamine
200801-70-3

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

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
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)-(+)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenol (R)-(-)-acetoxymandelic acid salt

(R)-(+)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenol (R)-(-)-acetoxymandelic acid salt

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
With potassium carbonate In water; toluene at 50 - 55℃;
(R)-3-(3-(diisopropylamino)-1-phenylpropyl)-4-hydroxybenzyl acetate
1390644-47-9

(R)-3-(3-(diisopropylamino)-1-phenylpropyl)-4-hydroxybenzyl acetate

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
With water; lithium hydroxide In methanol at 25 - 35℃; for 4h;
(R)-(4-(allyloxy)-3-(3-(diisopropylamino)-1-phenylpropyl)phenyl)methanol

(R)-(4-(allyloxy)-3-(3-(diisopropylamino)-1-phenylpropyl)phenyl)methanol

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0) In methanol at 25 - 30℃; for 2h;
(R)-N,N-diisopropyl-3-phenyl-3-(5-formyl-2-hydroxyphenyl)propyl-1-amine
214601-12-4

(R)-N,N-diisopropyl-3-phenyl-3-(5-formyl-2-hydroxyphenyl)propyl-1-amine

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol Product distribution / selectivity;74%
Stage #1: (R)-N,N-diisopropyl-3-phenyl-3-(5-formyl-2-hydroxyphenyl)propyl-1-amine With lithium aluminium tetrahydride In tetrahydrofuran for 2h;
Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran at 0℃; Product distribution / selectivity;		73%
C34H59NO2Si2

C34H59NO2Si2

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;92%
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanesulfonic acid / 50 - 55 °C / Inert atmosphere
2.1: ethanol / 20 - 60 °C / Inert atmosphere
3.1: sodium hydrogencarbonate / ethyl acetate / Inert atmosphere
3.2: 3.5 h / 20 °C
3.3: 0.5 h / -10 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: methanesulfonic acid / water / 50 - 55 °C / Inert atmosphere
2.1: ethanol / 60 °C / Inert atmosphere
3.1: sodium hydrogencarbonate / ethyl acetate / Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 20 °C
4.2: -10 °C
View Scheme
Multi-step reaction with 4 steps
1.1: methanesulfonic acid / 50 - 55 °C / Inert atmosphere
2.1: ethanol / 20 - 60 °C / Inert atmosphere
3.1: sodium hydrogencarbonate / ethyl acetate; water / Inert atmosphere
4.1: sodium hydroxide / methanol / 0 - 35 °C / Inert atmosphere
4.2: 4 h / 5 - 25 °C
4.3: 3 h / 0 - 5 °C
View Scheme
Multi-step reaction with 4 steps
1.1: methanesulfonic acid / 50 - 55 °C / Inert atmosphere
2.1: ethanol / 60 °C / Inert atmosphere
3.1: sodium hydrogencarbonate / ethyl acetate; water / Inert atmosphere
4.1: sodium hydroxide / methanol / 0 - 35 °C / Inert atmosphere
4.2: 5 - 25 °C
4.3: 3 h
View Scheme
Multi-step reaction with 4 steps
1.1: 1-methyl-piperazine / toluene / 25 - 110 °C
1.2: 5 h / 60 - 65 °C
2.1: hydrogen / 5%-palladium/activated carbon / methanol / 25 - 50 °C / 10343.2 Torr / Autoclave
3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0 - 30 °C / Inert atmosphere
4.1: D-Malic acid / isopropyl alcohol; di-isopropyl ether / 20 - 80 °C
4.2: pH 10
View Scheme
3-(N,N-diisopropylamino)-1-phenylpropan-1-ol
906532-26-1

3-(N,N-diisopropylamino)-1-phenylpropan-1-ol

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanesulfonic acid / 50 - 55 °C / Inert atmosphere
2.1: ethanol / 20 - 60 °C / Inert atmosphere
3.1: sodium hydrogencarbonate / ethyl acetate / Inert atmosphere
3.2: 3.5 h / 20 °C
3.3: 0.5 h / -10 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: methanesulfonic acid / water / 50 - 55 °C / Inert atmosphere
2.1: ethanol / 60 °C / Inert atmosphere
3.1: sodium hydrogencarbonate / ethyl acetate / Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 20 °C
4.2: -10 °C
View Scheme
Multi-step reaction with 4 steps
1.1: methanesulfonic acid / 50 - 55 °C / Inert atmosphere
2.1: ethanol / 20 - 60 °C / Inert atmosphere
3.1: sodium hydrogencarbonate / ethyl acetate; water / Inert atmosphere
4.1: sodium hydroxide / methanol / 0 - 35 °C / Inert atmosphere
4.2: 4 h / 5 - 25 °C
4.3: 3 h / 0 - 5 °C
View Scheme
Multi-step reaction with 4 steps
1.1: methanesulfonic acid / 50 - 55 °C / Inert atmosphere
2.1: ethanol / 60 °C / Inert atmosphere
3.1: sodium hydrogencarbonate / ethyl acetate; water / Inert atmosphere
4.1: sodium hydroxide / methanol / 0 - 35 °C / Inert atmosphere
4.2: 5 - 25 °C
4.3: 3 h
View Scheme
Multi-step reaction with 4 steps
1: perchloric acid / dichloromethane; water / 13 h / 40 °C / Inert atmosphere
2: sodium tetrahydroborate; calcium chloride / ethanol / 3 h / -10 - 20 °C / Inert atmosphere
3: tert-Amyl alcohol / 17 h / 20 - 70 °C / Inert atmosphere
4: potassium carbonate / water; toluene / 6 h / 50 °C / Inert atmosphere
View Scheme
methyl 4-(benzyloxy)-3-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]benzoate
156755-35-0

methyl 4-(benzyloxy)-3-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]benzoate

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C
2: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 50 - 55 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 3 h / Inert atmosphere
2: hydrogen / Raney nickel / methanol / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 5 h / 0 - 20 °C / Inert atmosphere
1.2: 0 - 5 °C
2.1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 25 - 35 °C / Autoclave
2.2: 25 - 35 °C
View Scheme
(+/-)-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropane-1-ol

(+/-)-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropane-1-ol

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C
2.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube
3.1: isopropyl alcohol / 15 h / 25 - 86 °C
4.1: sodium hydroxide / water
5.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux
5.2: 1 h / -65 - -60 °C
6.1: thionyl chloride / 10 °C / Reflux
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C
8.1: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 50 - 55 °C
View Scheme
Multi-step reaction with 7 steps
1.1: pyridine / dichloromethane / 5 - 30 °C / Industry scale
2.1: water / 75 - 78 °C / Industry scale
3.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 50 - 60 °C
3.2: -70 - -60 °C
3.3: -50 °C
4.1: borane-dimethyl sulfide complex / tetrahydrofuran / 25 - 50 °C
4.2: 0.5 h / 10 - 15 °C / Industry scale
5.1: raney nickel / methanol / 30 - 35 °C / Autoclave
6.1: tetrahydrofuran / 10 - 55 °C
7.1: potassium carbonate / toluene; water / 50 - 55 °C
View Scheme
Multi-step reaction with 7 steps
1.1: pyridine / dichloromethane / 5 - 30 °C / Industry scale
1.2: 5 - 30 °C / Industry scale
2.1: water / 75 - 78 °C / Industry scale
3.1: ethyl bromide; magnesium / iodine / tetrahydrofuran / 50 - 60 °C
3.2: -70 - -60 °C
4.1: dimethylsulfide borane complex / tetrahydrofuran / 25 - 50 °C
5.1: methanol / 30 - 35 °C
6.1: tetrahydrofuran / 10 - 55 °C
7.1: potassium carbonate / toluene; water / 50 - 55 °C
View Scheme
(+/-)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropylamine

(+/-)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropylamine

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: isopropyl alcohol / 15 h / 25 - 86 °C
2.1: sodium hydroxide / water
3.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux
3.2: 1 h / -65 - -60 °C
4.1: thionyl chloride / 10 °C / Reflux
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C
6.1: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 50 - 55 °C
View Scheme
Multi-step reaction with 5 steps
1.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 50 - 60 °C
1.2: -70 - -60 °C
1.3: -50 °C
2.1: borane-dimethyl sulfide complex / tetrahydrofuran / 25 - 50 °C
2.2: 0.5 h / 10 - 15 °C / Industry scale
3.1: raney nickel / methanol / 30 - 35 °C / Autoclave
4.1: tetrahydrofuran / 10 - 55 °C
5.1: potassium carbonate / toluene; water / 50 - 55 °C
View Scheme
Multi-step reaction with 5 steps
1.1: ethyl bromide; magnesium / iodine / tetrahydrofuran / 50 - 60 °C
1.2: -70 - -60 °C
2.1: dimethylsulfide borane complex / tetrahydrofuran / 25 - 50 °C
3.1: methanol / 30 - 35 °C
4.1: tetrahydrofuran / 10 - 55 °C
5.1: potassium carbonate / toluene; water / 50 - 55 °C
View Scheme
6-bromo-4-phenyl-3,4-dihydro-2H-chromen-2-one
156755-23-6

6-bromo-4-phenyl-3,4-dihydro-2H-chromen-2-one

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: potassium carbonate; sodium iodide / acetone / Reflux
2.1: sodium tetrahydroborate / 1,2-dimethoxyethane / 0.17 h
2.2: 3 h / 10 °C
3.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C
4.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube
5.1: isopropyl alcohol / 15 h / 25 - 86 °C
6.1: sodium hydroxide / water
7.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux
7.2: 1 h / -65 - -60 °C
8.1: thionyl chloride / 10 °C / Reflux
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C
10.1: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 50 - 55 °C
View Scheme
Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 35 °C / Industry scale
1.2: 5 - 30 °C / pH 1 - 2 / Industry scale
2.1: potassium carbonate / acetone / 20 - 25 °C / Industry scale
2.2: 50 - 60 °C
3.1: pyridine / dichloromethane / 5 - 30 °C / Industry scale
4.1: water / 75 - 78 °C / Industry scale
5.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 50 - 60 °C
5.2: -70 - -60 °C
5.3: -50 °C
6.1: borane-dimethyl sulfide complex / tetrahydrofuran / 25 - 50 °C
6.2: 0.5 h / 10 - 15 °C / Industry scale
7.1: raney nickel / methanol / 30 - 35 °C / Autoclave
8.1: tetrahydrofuran / 10 - 55 °C
9.1: potassium carbonate / toluene; water / 50 - 55 °C
View Scheme
Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 35 °C / Industry scale
1.2: 0 - 5 °C / Industry scale; Reflux
1.3: 0.5 h / 25 - 30 °C / pH 1 - 2 / Industry scale
2.1: potassium carbonate / acetone / 20 - 25 °C / Industry scale
2.2: 50 - 60 °C / Industry scale
3.1: pyridine / dichloromethane / 5 - 30 °C / Industry scale
3.2: 5 - 30 °C / Industry scale
4.1: water / 75 - 78 °C / Industry scale
5.1: ethyl bromide; magnesium / iodine / tetrahydrofuran / 50 - 60 °C
5.2: -70 - -60 °C
6.1: dimethylsulfide borane complex / tetrahydrofuran / 25 - 50 °C
7.1: methanol / 30 - 35 °C
8.1: tetrahydrofuran / 10 - 55 °C
9.1: potassium carbonate / toluene; water / 50 - 55 °C
View Scheme
(+/-)-toluene-4-sulphonic acid 3-(2-benzyloxy-5-bromophenyl)-3-phenylpropyl ester
250214-37-0

(+/-)-toluene-4-sulphonic acid 3-(2-benzyloxy-5-bromophenyl)-3-phenylpropyl ester

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube
2.1: isopropyl alcohol / 15 h / 25 - 86 °C
3.1: sodium hydroxide / water
4.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux
4.2: 1 h / -65 - -60 °C
5.1: thionyl chloride / 10 °C / Reflux
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C
7.1: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 50 - 55 °C
View Scheme
Multi-step reaction with 6 steps
1.1: water / 75 - 78 °C / Industry scale
2.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 50 - 60 °C
2.2: -70 - -60 °C
2.3: -50 °C
3.1: borane-dimethyl sulfide complex / tetrahydrofuran / 25 - 50 °C
3.2: 0.5 h / 10 - 15 °C / Industry scale
4.1: raney nickel / methanol / 30 - 35 °C / Autoclave
5.1: tetrahydrofuran / 10 - 55 °C
6.1: potassium carbonate / toluene; water / 50 - 55 °C
View Scheme
Multi-step reaction with 6 steps
1.1: water / 75 - 78 °C / Industry scale
2.1: ethyl bromide; magnesium / iodine / tetrahydrofuran / 50 - 60 °C
2.2: -70 - -60 °C
3.1: dimethylsulfide borane complex / tetrahydrofuran / 25 - 50 °C
4.1: methanol / 30 - 35 °C
5.1: tetrahydrofuran / 10 - 55 °C
6.1: potassium carbonate / toluene; water / 50 - 55 °C
View Scheme
methyl 3-[2-(benzyloxy)-5-bromophenyl]-3-phenylpropanoate
156755-24-7

methyl 3-[2-(benzyloxy)-5-bromophenyl]-3-phenylpropanoate

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / 1,2-dimethoxyethane / 0.17 h
1.2: 3 h / 10 °C
2.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C
3.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube
4.1: isopropyl alcohol / 15 h / 25 - 86 °C
5.1: sodium hydroxide / water
6.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux
6.2: 1 h / -65 - -60 °C
7.1: thionyl chloride / 10 °C / Reflux
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C
9.1: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 50 - 55 °C
View Scheme
Multi-step reaction with 8 steps
1.1: aluminum (III) chloride; sodium tetrahydroborate / 1,2-dimethoxyethane / 3.5 h / 0 - 10 °C
1.2: 0 - 5 °C
2.1: triethylamine / dichloromethane / 0.5 h / 20 - 30 °C
3.1: 25 - 112 °C / Autoclave
4.1: isopropyl alcohol / 14 h / 25 - 80 °C
5.1: sodium hydroxide / water / 0 - 35 °C / pH 9
6.1: magnesium / iodine / tetrahydrofuran / 1 h / -70 - 70 °C
6.2: -5 - 35 °C
6.3: pH 1 - 2
7.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 0 - 5 °C
8.1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 25 - 35 °C / Autoclave
8.2: 25 - 35 °C
View Scheme
Multi-step reaction with 8 steps
1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 5 - 10 °C / Inert atmosphere
2.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 5 °C
3.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere
4.1: isopropyl alcohol / 30 - 55 °C
5.1: sodium hydroxide; water / dichloromethane / 0.25 h / 10 - 20 °C / pH 11.5
5.2: 4 h / 25 - 55 °C / Inert atmosphere
5.3: -70 - -10 °C / Inert atmosphere
6.1: thionyl chloride / 5 h / 40 - 45 °C
7.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 0 - 5 °C / Inert atmosphere
8.1: hydrogen / 5%-palladium/activated carbon / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr
View Scheme
diisopropylamine
108-18-9

diisopropylamine

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate; potassium iodide / toluene; methanol / 20 h / Reflux
2.1: methanesulfonic acid / 3 h / 100 °C
3.1: sodium tetrahydroborate / methanol / 2 h / 0 °C
3.2: 0.08 h
3.3: pH 8
4.1: tert-Amyl alcohol / 25 - 70 °C
5.1: potassium carbonate / toluene; water / 1 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate; potassium iodide / toluene; methanol / 20 h / Reflux
2.1: methanesulfonic acid / 20 h / 120 °C
2.2: pH 7
2.3: 21 h / 100 °C
3.1: sodium tetrahydroborate / methanol / 2 h / 0 °C
3.2: 0.08 h
3.3: pH 8
4.1: tert-Amyl alcohol / 25 - 70 °C
5.1: potassium carbonate / toluene; water / 1 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate; potassium iodide / toluene; methanol / 20 h / Reflux
2.1: methanesulfonic acid / 23 h / 130 °C
2.2: pH 7
2.3: 4 h / 78 °C
3.1: sodium tetrahydroborate / methanol / 2 h / 0 °C
3.2: 0.08 h
3.3: pH 8
4.1: tert-Amyl alcohol / 25 - 70 °C
5.1: potassium carbonate / toluene; water / 1 h / 50 °C
View Scheme
(-)-N,N-Diisopropyl-3-(2-benzyloxy-5-carboxyphenyl)-3-phenylpropylamine hydrochloride

(-)-N,N-Diisopropyl-3-(2-benzyloxy-5-carboxyphenyl)-3-phenylpropylamine hydrochloride

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: borane-dimethyl sulfide complex / tetrahydrofuran / 25 - 50 °C
1.2: 0.5 h / 10 - 15 °C / Industry scale
2.1: raney nickel / methanol / 30 - 35 °C / Autoclave
3.1: tetrahydrofuran / 10 - 55 °C
4.1: potassium carbonate / toluene; water / 50 - 55 °C
View Scheme
Multi-step reaction with 4 steps
1: dimethylsulfide borane complex / tetrahydrofuran / 25 - 50 °C
2: methanol / 30 - 35 °C
3: tetrahydrofuran / 10 - 55 °C
4: potassium carbonate / toluene; water / 50 - 55 °C
View Scheme
Multi-step reaction with 6 steps
1: ammonia / ethyl acetate; water / pH 8 - 9
2: methanol / 50 - 65 °C
3: ammonia / water / pH 8 - 9
4: sulfuric acid / 20 °C / Reflux
5: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 3 h / Inert atmosphere
6: hydrogen / Raney nickel / methanol / 20 °C
View Scheme
Tolterodine acid
194482-44-5

Tolterodine acid

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Stage #1: Tolterodine acid With lithium aluminium tetrahydride In tetrahydrofuran for 2h;
Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran at 0℃; Product distribution / selectivity;
4-bromo-phenol
106-41-2

4-bromo-phenol

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: sulfuric acid / 120 - 125 °C
2.1: potassium carbonate; sodium iodide / acetone / Reflux
3.1: sodium tetrahydroborate / 1,2-dimethoxyethane / 0.17 h
3.2: 3 h / 10 °C
4.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C
5.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube
6.1: isopropyl alcohol / 15 h / 25 - 86 °C
7.1: sodium hydroxide / water
8.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux
8.2: 1 h / -65 - -60 °C
9.1: thionyl chloride / 10 °C / Reflux
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C
11.1: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 50 - 55 °C
View Scheme
Multi-step reaction with 10 steps
1.1: sulfuric acid / 4 h / 25 - 125 °C
2.1: potassium carbonate; sodium iodide / acetone / 2 h / 25 - 60 °C
3.1: aluminum (III) chloride; sodium tetrahydroborate / 1,2-dimethoxyethane / 3.5 h / 0 - 10 °C
3.2: 0 - 5 °C
4.1: triethylamine / dichloromethane / 0.5 h / 20 - 30 °C
5.1: 25 - 112 °C / Autoclave
6.1: isopropyl alcohol / 14 h / 25 - 80 °C
7.1: sodium hydroxide / water / 0 - 35 °C / pH 9
8.1: magnesium / iodine / tetrahydrofuran / 1 h / -70 - 70 °C
8.2: -5 - 35 °C
8.3: pH 1 - 2
9.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 0 - 5 °C
10.1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 25 - 35 °C / Autoclave
10.2: 25 - 35 °C
View Scheme
Multi-step reaction with 10 steps
1.1: sulfuric acid / 12 h / 120 - 125 °C
2.1: potassium carbonate; sodium iodide / acetone / 25 - 30 °C
2.2: 5.5 h / 15 °C / Reflux
3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 5 - 10 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 5 °C
5.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere
6.1: isopropyl alcohol / 30 - 55 °C
7.1: sodium hydroxide; water / dichloromethane / 0.25 h / 10 - 20 °C / pH 11.5
7.2: 4 h / 25 - 55 °C / Inert atmosphere
7.3: -70 - -10 °C / Inert atmosphere
8.1: thionyl chloride / 5 h / 40 - 45 °C
9.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 0 - 5 °C / Inert atmosphere
10.1: hydrogen / 5%-palladium/activated carbon / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr
View Scheme
Multi-step reaction with 10 steps
1.1: sulfuric acid / 12 h / 120 - 125 °C
2.1: potassium carbonate; sodium iodide / acetone / 25 - 30 °C
2.2: 5.5 h / 15 °C / Reflux
3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 5 - 10 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 5 °C
5.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere
6.1: isopropyl alcohol / 30 - 55 °C
7.1: sodium hydroxide; water / dichloromethane / 0.25 h / 10 - 20 °C / pH 11.5
7.2: 4 h / 25 - 55 °C / Inert atmosphere
7.3: -70 - -10 °C / Inert atmosphere
8.1: thionyl chloride / 5 h / 40 - 45 °C
9.1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 18 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave
10.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 2 h / 0 - 5 °C / Inert atmosphere
View Scheme
(R)-4-(benzyloxy)-3-(3-(diisopropylamino)-1-phenylpropyl)benzoic acid hydrochloride
156755-33-8

(R)-4-(benzyloxy)-3-(3-(diisopropylamino)-1-phenylpropyl)benzoic acid hydrochloride

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / 10 °C / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C
3: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 50 - 55 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 0 - 5 °C
2.1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 25 - 35 °C / Autoclave
2.2: 25 - 35 °C
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride / 5 h / 40 - 45 °C
2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 0 - 5 °C / Inert atmosphere
3: hydrogen / 5%-palladium/activated carbon / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride / 5 h / 40 - 45 °C
2: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 18 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave
3: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 2 h / 0 - 5 °C / Inert atmosphere
View Scheme
R-(-)-[3-(2-benzyloxy-5-bromophenyl)-3-phenylpropyl]diisopropylamine
950773-38-3

R-(-)-[3-(2-benzyloxy-5-bromophenyl)-3-phenylpropyl]diisopropylamine

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux
1.2: 1 h / -65 - -60 °C
2.1: thionyl chloride / 10 °C / Reflux
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C
4.1: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 50 - 55 °C
View Scheme
Multi-step reaction with 3 steps
1.1: magnesium / iodine / tetrahydrofuran / 1 h / -70 - 70 °C
1.2: -5 - 35 °C
1.3: pH 1 - 2
2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 0 - 5 °C
3.1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 25 - 35 °C / Autoclave
3.2: 25 - 35 °C
View Scheme
Multi-step reaction with 4 steps
1.1: iodine; magnesium; ethyl bromide / tetrahydrofuran / 2 h / 60 - 65 °C / Inert atmosphere
1.2: 1 h / -70 - -50 °C
2.1: thionyl chloride / 0 - 65 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C
4.1: hydrogen; palladium 10% on activated carbon / isopropyl alcohol / 25 - 30 °C / 2068.65 - 2585.81 Torr / Autoclave
View Scheme
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 1-methyl-piperazine / toluene / 25 - 110 °C
1.2: 5 h / 60 - 65 °C
2.1: hydrogen / 5%-palladium/activated carbon / methanol / 25 - 50 °C / 10343.2 Torr / Autoclave
3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0 - 30 °C / Inert atmosphere
4.1: D-Malic acid / isopropyl alcohol; di-isopropyl ether / 20 - 80 °C
4.2: pH 10
View Scheme
Multi-step reaction with 4 steps
1.1: 1-methyl-piperazine / toluene / Heating
1.2: 5 h / Reflux
2.1: methanol / 1.25 h / 40 °C / Inert atmosphere
2.2: 20 h / 40 °C / 5948.09 Torr / Inert atmosphere
3.1: tert-Amyl alcohol / 70 °C / Resolution of racemate; Large scale reaction
4.1: potassium carbonate / water; toluene / 6 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 1-methyl-piperazine / toluene / Heating
1.2: 5 h / Reflux
2.1: 5%-palladium/activated carbon; hydrogen / tert-Amyl alcohol / 80 °C / 5171.62 Torr
3.1: tert-Amyl alcohol / 70 °C / Resolution of racemate; Large scale reaction
4.1: potassium carbonate / water; toluene / 6 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 1-methyl-piperazine / toluene / Heating
1.2: 5 h / Reflux
2.1: titanium(IV)isopropoxide / tetrahydrofuran / 1 h / Reflux
2.2: 20 °C
3.1: tert-Amyl alcohol / 70 °C / Resolution of racemate; Large scale reaction
4.1: potassium carbonate / water; toluene / 6 h / 50 °C
View Scheme
formic acid
64-18-6

formic acid

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

(R)-(+)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenol formate
380636-49-7

(R)-(+)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenol formate

Conditions
ConditionsYield
In acetonitrile at 20℃;100%
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

(R)-5-hydroxymethyl tolterodine fumarate salt
380636-50-0

(R)-5-hydroxymethyl tolterodine fumarate salt

Conditions
ConditionsYield
In acetone at 20℃; for 0.5h;100%
In acetone at 25 - 30℃; for 1h;2.4 g
isobutyryl chloride
79-30-1

isobutyryl chloride

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

fesoterodine
286930-02-7

fesoterodine

Conditions
ConditionsYield
With sodium hydroxide In water; toluene at 20℃; Product distribution / selectivity; Inert atmosphere;98%
With sodium hydroxide In water; toluene at 20℃; for 0.166667h; Product distribution / selectivity; Inert atmosphere;98%
With sodium hydroxide In water; toluene at 20℃; Inert atmosphere;98%
isobutyryl chloride
79-30-1

isobutyryl chloride

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

(R)-(+)-2-(3-diisopropylamino-1-phenyl-propyl)-4-hydroxymethyl-phenyl isobutyrate

(R)-(+)-2-(3-diisopropylamino-1-phenyl-propyl)-4-hydroxymethyl-phenyl isobutyrate

Conditions
ConditionsYield
With sodium hydroxide In water; toluene at 20℃; for 0.166667h; Inert atmosphere;98%
isobutyryl chloride
79-30-1

isobutyryl chloride

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

[2-[(1R)-3-(di(propan-2-yl)amino)-1-phenylpropyl]-4-(hydroxymethyl)phenyl]-2-methylpropanoate fumarate

[2-[(1R)-3-(di(propan-2-yl)amino)-1-phenylpropyl]-4-(hydroxymethyl)phenyl]-2-methylpropanoate fumarate

Conditions
ConditionsYield
Stage #1: isobutyryl chloride; (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol With triethylamine In dichloromethane at 0 - 30℃; for 0.75h;
Stage #2: (2E)-but-2-enedioic acid In cyclohexane; butanone at 0 - 20℃;		71%
...Expand
isobutyryl chloride
79-30-1

isobutyryl chloride

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

A

fesoterodine
286930-02-7

fesoterodine

B

C30H43NO4
1208313-13-6

C30H43NO4

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃; for 2.5h; Product distribution / selectivity;
With triethylamine In dichloromethane at -10 - -5℃; for 2.5h; Product distribution / selectivity;
Stage #1: isobutyryl chloride; (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol In dichloromethane at -10 - -5℃; for 2.5h;
Stage #2: With sodium carbonate In dichloromethane; water Product distribution / selectivity;
...Expand
(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

(3R)-3-[2-hydroxy-5-(hydroxymethyl)phenyl]-N,N-diisopropyl-N-methyl-3-phenylpropane-1-aminium iodide

(3R)-3-[2-hydroxy-5-(hydroxymethyl)phenyl]-N,N-diisopropyl-N-methyl-3-phenylpropane-1-aminium iodide

(S)-Mandelic acid
17199-29-0

(S)-Mandelic acid

isobutyryl chloride
79-30-1

isobutyryl chloride

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol
207679-81-0

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

2-[(1R)-3-[bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxy-methylphenyl isobutyrate mandelate
1206695-46-6

2-[(1R)-3-[bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxy-methylphenyl isobutyrate mandelate

Conditions
ConditionsYield
Stage #1: isobutyryl chloride; (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol In dichloromethane at -10 - 0℃;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water for 0.25h;
Stage #3: (S)-Mandelic acid In isopropyl alcohol at 10 - 55℃; for 7.5h;
...Expand

(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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