Product Name

  • Name

    N-[2-Hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl)propan-2-ylamino]ethyl]phenyl]formamide

  • EINECS
  • CAS No. 73573-87-2
  • Article Data13
  • CAS DataBase
  • Density 1.233 g/cm3
  • Solubility DMSO: 20 mg/mL, soluble in water
  • Melting Point
  • Formula C19H24N2O4
  • Boiling Point 603.2 °C at 760 mmHg
  • Molecular Weight 344.411
  • Flash Point 318.6 °C
  • Transport Information
  • Appearance off-white solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 73573-87-2 (N-[2-Hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl)propan-2-ylamino]ethyl]phenyl]formamide)
  • Hazard Symbols
  • Synonyms Eformoterol;Formamide,N-[2-hydroxy-5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-,(R*,R*)-;Formatris Novolizer;Oxis;
  • PSA 90.82000
  • LogP 3.32310

Synthetic route

N-[5-[(1R)-Hydroxy-2-[[(1R)-methyl-2-(4-methoxyphenyl)ethyl](phenylmethyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-formamide
188690-83-7

N-[5-[(1R)-Hydroxy-2-[[(1R)-methyl-2-(4-methoxyphenyl)ethyl](phenylmethyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-formamide

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In ethanol at 25 - 30℃; under 2942.29 Torr; for 3h;80%
With hydrogen; palladium on activated charcoal In ethanol
With hydrogen; palladium 10% on activated carbon In methanol
With palladium 10% on activated carbon; hydrogen In isopropyl alcohol at 35 - 36℃; Autoclave;
N-(2-Benzyloxy-5-{(R)-1-hydroxy-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide
408497-91-6

N-(2-Benzyloxy-5-{(R)-1-hydroxy-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
With hydrogen; 10% palladium on active carbon In ethanol at 20℃; Hydrogenolysis;
2-amino-1-(4-methyoxyphenyl)propane
64-13-1

2-amino-1-(4-methyoxyphenyl)propane

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: Candida antarctica lipase B
2: 3M aq. KOH / Heating
3: dimethylsulfoxide / 87 h / 80 °C
4: neutral Al2O3 (activity III)
5: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
6: 69 percent / pyridine / 6.5 h / 60 °C
7: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene
37629-51-9

1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 78 percent / LiAlH4 / diethyl ether / 2 h / Heating
2: Candida antarctica lipase B
3: 3M aq. KOH / Heating
4: dimethylsulfoxide / 87 h / 80 °C
5: neutral Al2O3 (activity III)
6: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
7: 69 percent / pyridine / 6.5 h / 60 °C
8: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: LiAlH4 / diethyl ether / 2 h / Heating
1.2: Candida antarctica lipase B; ethyl acetate; Et3N / 4 h / 30 °C
2.1: dimethylsulfoxide / 87 h / 80 °C
3.1: neutral Al2O3 (activity III)
4.1: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
5.1: 69 percent / pyridine / 6.5 h / 60 °C
6.1: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
4-benzyloxy-3-nitroacetophenone
14347-05-8

4-benzyloxy-3-nitroacetophenone

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 82 percent / Br2 / CHCl3 / 25 °C
2: 87 percent / BH3*THF / tetrahydrofuran / -20 °C
3: lipase PS Celite-immobilized / various solvent(s) / 72 h / 37 °C
4: K2CO3 / methanol / 2.5 h / 20 °C
5: dimethylsulfoxide / 87 h / 80 °C
6: neutral Al2O3 (activity III)
7: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
8: 69 percent / pyridine / 6.5 h / 60 °C
9: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: 82 percent / Br2 / CHCl3 / 25 °C
2.1: BH3*THF / tetrahydrofuran / -20 °C
2.2: 48 percent / lipase PS; vinyl acetate / various solvent(s) / 72 h / 37 °C
3.1: K2CO3 / methanol / 2.5 h / 20 °C
4.1: dimethylsulfoxide / 87 h / 80 °C
5.1: neutral Al2O3 (activity III)
6.1: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
7.1: 69 percent / pyridine / 6.5 h / 60 °C
8.1: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
4-benzyloxy-3-nitrophenacyl bromide
43229-01-2

4-benzyloxy-3-nitrophenacyl bromide

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 87 percent / BH3*THF / tetrahydrofuran / -20 °C
2: lipase PS Celite-immobilized / various solvent(s) / 72 h / 37 °C
3: K2CO3 / methanol / 2.5 h / 20 °C
4: dimethylsulfoxide / 87 h / 80 °C
5: neutral Al2O3 (activity III)
6: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
7: 69 percent / pyridine / 6.5 h / 60 °C
8: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: BH3*THF / tetrahydrofuran / -20 °C
1.2: 48 percent / lipase PS; vinyl acetate / various solvent(s) / 72 h / 37 °C
2.1: K2CO3 / methanol / 2.5 h / 20 °C
3.1: dimethylsulfoxide / 87 h / 80 °C
4.1: neutral Al2O3 (activity III)
5.1: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
6.1: 69 percent / pyridine / 6.5 h / 60 °C
7.1: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: 98 percent / oxazaborolidine from cis (1R,2S)-aminoindanol and trimethylboroxine, BH3 / tetrahydrofuran / -15 °C
2: 98 percent / aqueous sodium hydroxide / methanol / 0.5 h
3: 90 °C
4: H2 / PtO2
6: H2 / Pd-C / ethanol
View Scheme
(R)-(-)-p-methoxyamphetamine
58993-79-6

(R)-(-)-p-methoxyamphetamine

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dimethylsulfoxide / 87 h / 80 °C
2: neutral Al2O3 (activity III)
3: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
4: 69 percent / pyridine / 6.5 h / 60 °C
5: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(E/Z)-crotylstannane(1-)*Et4N(1+)

(E/Z)-crotylstannane(1-)*Et4N(1+)

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 81 percent / ammonium acetate / 0.58 h / Heating
2: 78 percent / LiAlH4 / diethyl ether / 2 h / Heating
3: Candida antarctica lipase B
4: 3M aq. KOH / Heating
5: dimethylsulfoxide / 87 h / 80 °C
6: neutral Al2O3 (activity III)
7: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
8: 69 percent / pyridine / 6.5 h / 60 °C
9: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 81 percent / ammonium acetate / 0.58 h / Heating
2.1: LiAlH4 / diethyl ether / 2 h / Heating
2.2: Candida antarctica lipase B; ethyl acetate; Et3N / 4 h / 30 °C
3.1: dimethylsulfoxide / 87 h / 80 °C
4.1: neutral Al2O3 (activity III)
5.1: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
6.1: 69 percent / pyridine / 6.5 h / 60 °C
7.1: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
(+/-)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol
299964-35-5

(+/-)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: lipase PS Celite-immobilized / various solvent(s) / 72 h / 37 °C
2: K2CO3 / methanol / 2.5 h / 20 °C
3: dimethylsulfoxide / 87 h / 80 °C
4: neutral Al2O3 (activity III)
5: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
6: 69 percent / pyridine / 6.5 h / 60 °C
7: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
(R)-1-(4-benzyloxy-3-nitrophenyl)oxirane
188730-94-1

(R)-1-(4-benzyloxy-3-nitrophenyl)oxirane

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dimethylsulfoxide / 87 h / 80 °C
2: neutral Al2O3 (activity III)
3: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
4: 69 percent / pyridine / 6.5 h / 60 °C
5: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 90 °C
2: H2 / PtO2
4: H2 / Pd-C / ethanol
View Scheme
Multi-step reaction with 4 steps
1.1: 20 h / 140 °C / Inert atmosphere
2.1: hydrogen / Ni-Raney / isopropyl alcohol; toluene / 20 h / 40 °C / 13680.9 Torr
3.1: acetic anhydride / 2 h / 50 °C / Inert atmosphere
3.2: 1 h / 0 °C
3.3: 0.25 h / 0 °C
4.1: hydrogen / 5% Pd(II)/C(eggshell) / ethanol / 20 h / 40 °C / 7600.51 Torr
View Scheme
Multi-step reaction with 4 steps
1.1: 10 h / 20 - 110 °C
2.1: water; sodium dithionite / di-isopropyl ether; acetone; methanol / 20 - 60 °C
2.2: 25 - 60 °C / pH 9 - 9.5
3.1: polyethylene glycol-400 / 20 - 65 °C
3.2: pH 7 - 7.5
4.1: hydrogen / palladium 10% on activated carbon / methanol
View Scheme
(R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol
188690-82-6

(R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: K2CO3 / methanol / 2.5 h / 20 °C
2: dimethylsulfoxide / 87 h / 80 °C
3: neutral Al2O3 (activity III)
4: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
5: 69 percent / pyridine / 6.5 h / 60 °C
6: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: 98 percent / aqueous sodium hydroxide / methanol / 0.5 h
2: 90 °C
3: H2 / PtO2
5: H2 / Pd-C / ethanol
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate / toluene; methanol / 20 h / 40 °C
2.1: 20 h / 140 °C / Inert atmosphere
3.1: hydrogen / Ni-Raney / isopropyl alcohol; toluene / 20 h / 40 °C / 13680.9 Torr
4.1: acetic anhydride / 2 h / 50 °C / Inert atmosphere
4.2: 1 h / 0 °C
4.3: 0.25 h / 0 °C
5.1: hydrogen / 5% Pd(II)/C(eggshell) / ethanol / 20 h / 40 °C / 7600.51 Torr
View Scheme
(R)-N-[1-(o-methoxyphenyl)propan-2-yl]ethanamide
86073-42-9

(R)-N-[1-(o-methoxyphenyl)propan-2-yl]ethanamide

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 3M aq. KOH / Heating
2: dimethylsulfoxide / 87 h / 80 °C
3: neutral Al2O3 (activity III)
4: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
5: 69 percent / pyridine / 6.5 h / 60 °C
6: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Acetic acid (S)-1-(4-benzyloxy-3-nitro-phenyl)-2-bromo-ethyl ester
299964-37-7

Acetic acid (S)-1-(4-benzyloxy-3-nitro-phenyl)-2-bromo-ethyl ester

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: K2CO3 / methanol / 2.5 h / 20 °C
2: dimethylsulfoxide / 87 h / 80 °C
3: neutral Al2O3 (activity III)
4: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
5: 69 percent / pyridine / 6.5 h / 60 °C
6: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
(R)-1-(3-Amino-4-benzyloxy-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol
299964-43-5

(R)-1-(3-Amino-4-benzyloxy-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 69 percent / pyridine / 6.5 h / 60 °C
2: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
(R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol
245759-61-9

(R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
2: 69 percent / pyridine / 6.5 h / 60 °C
3: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
[(R)-2-(4-Benzyloxy-3-nitro-phenyl)-2-trimethylsilanyloxy-ethyl]-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethyl]-amine

[(R)-2-(4-Benzyloxy-3-nitro-phenyl)-2-trimethylsilanyloxy-ethyl]-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethyl]-amine

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: neutral Al2O3 (activity III)
2: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
3: 69 percent / pyridine / 6.5 h / 60 °C
4: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
4-methoxybenzyl methyl ketone
122-84-9

4-methoxybenzyl methyl ketone

1-<4-methoxy-phenyl>-propanol-(2)

1-<4-methoxy-phenyl>-propanol-(2)

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: H2 / Pt-C / ethanol
2: 90 °C
3: H2 / PtO2
5: H2 / Pd-C / ethanol
View Scheme
(R)-(-)-1-(4'-methoxyphenyl)-2-benzylaminopropane
67346-60-5

(R)-(-)-1-(4'-methoxyphenyl)-2-benzylaminopropane

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 °C
2: H2 / PtO2
4: H2 / Pd-C / ethanol
View Scheme
Multi-step reaction with 4 steps
1.1: 10 h / 20 - 110 °C
2.1: water; sodium dithionite / di-isopropyl ether; acetone; methanol / 20 - 60 °C
2.2: 25 - 60 °C / pH 9 - 9.5
3.1: polyethylene glycol-400 / 20 - 65 °C
3.2: pH 7 - 7.5
4.1: hydrogen / palladium 10% on activated carbon / methanol
View Scheme
Multi-step reaction with 2 steps
1: 12 h / 90 - 110 °C
2: palladium 10% on activated carbon; hydrogen / isopropyl alcohol / 35 - 36 °C / Autoclave
View Scheme
Multi-step reaction with 5 steps
1: potassium carbonate; potassium iodide / acetone / 3 h / 25 - 30 °C
2: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / -10 - -5 °C
3: ammonium formate / palladium 10% on activated carbon / N,N-dimethyl-formamide / 2 h / 40 - 75 °C
4: acetic anhydride / tetrahydrofuran; toluene / 15 - 30 °C
5: hydrogen / palladium 10% on activated carbon / ethanol / 3 h / 25 - 30 °C / 2942.29 Torr
View Scheme
(R,R)-3-amino-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenyl methyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol
289657-26-7

(R,R)-3-amino-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenyl methyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: H2 / Pd-C / ethanol
View Scheme
Multi-step reaction with 2 steps
1.1: polyethylene glycol-400 / 20 - 65 °C
1.2: pH 7 - 7.5
2.1: hydrogen / palladium 10% on activated carbon / methanol
View Scheme
Multi-step reaction with 2 steps
1: acetic anhydride / tetrahydrofuran; toluene / 15 - 30 °C
2: hydrogen / palladium 10% on activated carbon / ethanol / 3 h / 25 - 30 °C / 2942.29 Torr
View Scheme
(R,R)-3-nitro-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol
245759-65-3

(R,R)-3-nitro-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2 / PtO2
3: H2 / Pd-C / ethanol
View Scheme
Multi-step reaction with 3 steps
1.1: water; sodium dithionite / di-isopropyl ether; acetone; methanol / 20 - 60 °C
1.2: 25 - 60 °C / pH 9 - 9.5
2.1: polyethylene glycol-400 / 20 - 65 °C
2.2: pH 7 - 7.5
3.1: hydrogen / palladium 10% on activated carbon / methanol
View Scheme
Multi-step reaction with 3 steps
1: ammonium formate / palladium 10% on activated carbon / N,N-dimethyl-formamide / 2 h / 40 - 75 °C
2: acetic anhydride / tetrahydrofuran; toluene / 15 - 30 °C
3: hydrogen / palladium 10% on activated carbon / ethanol / 3 h / 25 - 30 °C / 2942.29 Torr
View Scheme
(R,R)-N-(2-benzyloxy-5-{1-hydroxy-2-[[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amino]-ethyl}-phenyl)-formamide
1316100-17-0

(R,R)-N-(2-benzyloxy-5-{1-hydroxy-2-[[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amino]-ethyl}-phenyl)-formamide

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
With 5% Pd(II)/C(eggshell); hydrogen In methanol under 2327.23 Torr; for 12h;5.57 g
With hydrogen; 5% Pd(II)/C(eggshell) In ethanol at 40℃; under 7600.51 Torr; for 20h; Product distribution / selectivity;n/a
4-methoxybenzyl methyl ketone
122-84-9

4-methoxybenzyl methyl ketone

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogen / platinum on carbon / methanol / 20 h / 30 °C / 7600.51 Torr
2.1: hydrogenchloride / water; acetone / 1 h / 0 - 23 °C
3.1: 20 h / 140 °C / Inert atmosphere
4.1: hydrogen / Ni-Raney / isopropyl alcohol; toluene / 20 h / 40 °C / 13680.9 Torr
5.1: acetic anhydride / 2 h / 50 °C / Inert atmosphere
5.2: 1 h / 0 °C
5.3: 0.25 h / 0 °C
6.1: hydrogen / 5% Pd(II)/C(eggshell) / ethanol / 20 h / 40 °C / 7600.51 Torr
View Scheme
Multi-step reaction with 7 steps
1.1: 1,2-dichloro-ethane / 2 h / 20 - 40 °C
2.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 3 h / 5 - 25 °C
3.1: tetrahydrofuran / 50 - 55 °C / Resolution of racemate
4.1: 10 h / 20 - 110 °C
5.1: water; sodium dithionite / di-isopropyl ether; acetone; methanol / 20 - 60 °C
5.2: 25 - 60 °C / pH 9 - 9.5
6.1: polyethylene glycol-400 / 20 - 65 °C
6.2: pH 7 - 7.5
7.1: hydrogen / palladium 10% on activated carbon / methanol
View Scheme
Multi-step reaction with 6 steps
1.1: tetrahydrofuran / 2 h / 20 - 40 °C / Autoclave
1.2: 20 - 30 °C
2.1: tetrahydrofuran / 50 - 55 °C / Resolution of racemate
3.1: 10 h / 20 - 110 °C
4.1: water; sodium dithionite / di-isopropyl ether; acetone; methanol / 20 - 60 °C
4.2: 25 - 60 °C / pH 9 - 9.5
5.1: polyethylene glycol-400 / 20 - 65 °C
5.2: pH 7 - 7.5
6.1: hydrogen / palladium 10% on activated carbon / methanol
View Scheme
(R)-1-(4-methoxyphenyl)-N-((R)-1-phenylethyl)propan-2-amine
140173-30-4

(R)-1-(4-methoxyphenyl)-N-((R)-1-phenylethyl)propan-2-amine

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 20 h / 140 °C / Inert atmosphere
2.1: hydrogen / Ni-Raney / isopropyl alcohol; toluene / 20 h / 40 °C / 13680.9 Torr
3.1: acetic anhydride / 2 h / 50 °C / Inert atmosphere
3.2: 1 h / 0 °C
3.3: 0.25 h / 0 °C
4.1: hydrogen / 5% Pd(II)/C(eggshell) / ethanol / 20 h / 40 °C / 7600.51 Torr
View Scheme
[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amine

[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amine

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water; acetone / 1 h / 0 - 23 °C
2.1: 20 h / 140 °C / Inert atmosphere
3.1: hydrogen / Ni-Raney / isopropyl alcohol; toluene / 20 h / 40 °C / 13680.9 Torr
4.1: acetic anhydride / 2 h / 50 °C / Inert atmosphere
4.2: 1 h / 0 °C
4.3: 0.25 h / 0 °C
5.1: hydrogen / 5% Pd(II)/C(eggshell) / ethanol / 20 h / 40 °C / 7600.51 Torr
View Scheme
(R,R)-1-(4-benzyloxy-3-nitro-phenyl)-2-[[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amino]-ethanol
1262020-50-7

(R,R)-1-(4-benzyloxy-3-nitro-phenyl)-2-[[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amino]-ethanol

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogen / Ni-Raney / isopropyl alcohol; toluene / 20 h / 40 °C / 13680.9 Torr
2.1: acetic anhydride / 2 h / 50 °C / Inert atmosphere
2.2: 1 h / 0 °C
2.3: 0.25 h / 0 °C
3.1: hydrogen / 5% Pd(II)/C(eggshell) / ethanol / 20 h / 40 °C / 7600.51 Torr
View Scheme
[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amine
43229-65-8

[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amine

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrahydrofuran / 50 - 55 °C / Resolution of racemate
2.1: 10 h / 20 - 110 °C
3.1: water; sodium dithionite / di-isopropyl ether; acetone; methanol / 20 - 60 °C
3.2: 25 - 60 °C / pH 9 - 9.5
4.1: polyethylene glycol-400 / 20 - 65 °C
4.2: pH 7 - 7.5
5.1: hydrogen / palladium 10% on activated carbon / methanol
View Scheme
Multi-step reaction with 2 steps
1.1: methanol / 20 °C / Inert atmosphere; Reflux
2.1: potassium carbonate / methanol; tetrahydrofuran / 25 °C / Inert atmosphere
2.2: 255 / 24 h / 120 °C / Inert atmosphere
2.3: 25 °C / 2327.23 Torr / Inert atmosphere
View Scheme
C17H19NO
1096141-37-5

C17H19NO

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 3 h / 5 - 25 °C
2.1: tetrahydrofuran / 50 - 55 °C / Resolution of racemate
3.1: 10 h / 20 - 110 °C
4.1: water; sodium dithionite / di-isopropyl ether; acetone; methanol / 20 - 60 °C
4.2: 25 - 60 °C / pH 9 - 9.5
5.1: polyethylene glycol-400 / 20 - 65 °C
5.2: pH 7 - 7.5
6.1: hydrogen / palladium 10% on activated carbon / methanol
View Scheme
N-[5-((1R)-2-bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]carboxamide
201677-59-0

N-[5-((1R)-2-bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]carboxamide

(R)-N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)amine L-mandelate

(R)-N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)amine L-mandelate

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Stage #1: N-[5-((1R)-2-bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]carboxamide; (R)-N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)amine L-mandelate With potassium carbonate In tetrahydrofuran; methanol at 25℃; Inert atmosphere;
Stage #2: at 120℃; for 24h; Inert atmosphere;
Stage #3: With palladium 10% on activated carbon; hydrogen In ethanol at 25℃; under 2327.23 Torr; Inert atmosphere;		n/a
(1R)-1-[3-amino-4-(phenylmethoxy)phenyl]-2-bromoethan-1-ol
333796-54-6

(1R)-1-[3-amino-4-(phenylmethoxy)phenyl]-2-bromoethan-1-ol

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic anhydride / 0 - 5 °C / Inert atmosphere
1.2: 1 h / 0 - 5 °C / Inert atmosphere
2.1: 12 h / 90 - 110 °C
3.1: palladium 10% on activated carbon; hydrogen / isopropyl alcohol / 35 - 36 °C / Autoclave
View Scheme
Multi-step reaction with 4 steps
1.1: acetic anhydride / 0 - 5 °C
1.2: 1 h / 0 - 5 °C / Inert atmosphere
2.1: potassium carbonate / tetrahydrofuran; methanol / 2 h / 25 - 30 °C / Inert atmosphere; Large scale
3.1: 12 h / 90 - 110 °C
4.1: palladium 10% on activated carbon; hydrogen / isopropyl alcohol / 35 - 36 °C / Autoclave
View Scheme
L-Tartaric acid
87-69-4

L-Tartaric acid

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

(R,R)-formoterol L-tartrate

(R,R)-formoterol L-tartrate

Conditions
ConditionsYield
In methanol; acetonitrile at 23℃; for 1h; Solvent; Temperature; Time;91%
In water; isopropyl alcohol; toluene at 20 - 45℃; for 5.5h;70%
In water; isopropyl alcohol; toluene
In water; toluene at 25 - 30℃; for 3h; Inert atmosphere;68 g
L-Tartaric acid
87-69-4

L-Tartaric acid

(R,R)-formoterol
73573-87-2

(R,R)-formoterol

(R,R)-formoterol-L-tartrate

(R,R)-formoterol-L-tartrate

Conditions
ConditionsYield
In ethanol; water; isopropyl alcohol at 20 - 80℃; Product distribution / selectivity;

Formoterol Specification

The Formamide,N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-,rel-, with CAS registry number 73573-87-2, belongs to the following product category: (intermediates of formoterol ). It has the systematic name of N-{2-hydroxy-5-[(1R)-1-hydroxy-2-{[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl]phenyl}formamide. This chemical is a kind of off-white solid. And the chemical formula of this chemical is C19H24N2O4.

Physical properties of Formamide,N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-,rel-: (1)ACD/LogP: 1.57; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.4; (4)ACD/LogD (pH 7.4): -0.07; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 3.93; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 51.24 Å2; (13)Index of Refraction: 1.616; (14)Molar Refractivity: 97.63 cm3; (15)Molar Volume: 279.1 cm3; (16)Polarizability: 38.7×10-24cm3; (17)Surface Tension: 53.6 dyne/cm; (18)Density: 1.233 g/cm3; (19)Flash Point: 318.6 °C; (20)Enthalpy of Vaporization: 94.35 kJ/mol; (21)Boiling Point: 603.2 °C at 760 mmHg; (22)Vapour Pressure: 2.12E-15 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=CNc1cc(ccc1O)[C@@H](O)CN[C@H](C)Cc2ccc(OC)cc2
(2)InChI: InChI=1/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1
(3)InChIKey: BPZSYCZIITTYBL-YJYMSZOUBO
(4)Std. InChI: InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1
(5)Std. InChIKey: BPZSYCZIITTYBL-YJYMSZOUSA-N

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