115290-81-8

Basic information

• Product Name: (R)-(+)-3-(N-METHYLAMINO)-1-PHENYL-1-PROPANOL
• Synonyms: (R)-3-(methylamino)-1-phenylpropanol;(1R)-(+)-3-(Methylamino)-1-phenylpropan-1-ol;(3R)-N-Methyl-3-hydroxy-3-phenylpropylamine;(R)-3-Hydroxy-N-methyl-3-phenylpropylamine;(R)-N-Methyl-3-hydroxy-3-phenylpropylamine;(R)-N-Methyl-3-phenyl-3-hydroxypropylamine;Atomoxetine Related Compound A (10 mg) (3-(Methylamino)-1-phenylpropan-1-ol);Destolyl Atomoxetine
• CAS NO: 115290-81-8
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• Mol File: 115290-81-8.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 286℃
• Flash Point: 115℃
• Appearance: /
• Density: 1.017
• Vapor Pressure: 0.00126mmHg at 25°C
• Refractive Index: 1.53
• PKA: 14.24±0.20(Predicted)
• CAS DataBase Reference: (R)-(+)-3-(N-METHYLAMINO)-1-PHENYL-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-3-(N-METHYLAMINO)-1-PHENYL-1-PROPANOL(115290-81-8)
• EPA Substance Registry System: (R)-(+)-3-(N-METHYLAMINO)-1-PHENYL-1-PROPANOL(115290-81-8)

Safety Data

• Hazardous Substances Data: 115290-81-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 115290-81-8 differently. You can refer to the following data:
1. Destolyl Atomoxetine is a metabolitte of Atomoxetine (A791400), a norepinephrine reuptake inhibitor.
2. Sitagliptin phosphate intermediate
3. Destolyl Atomoxetine (Atomoxetine EP Impurity H) is a metabolitte of Atomoxetine (A791400), a norepinephrine reuptake inhibitor.

InChI:InChI=1/C10H15NO/c1-11-8-7-10(12)9-5-3-2-4-6-9/h2-6,10-12H,7-8H2,1H3/t10-/m1/s1

Synthetic route

(R)-3-iodo-1-phenyl-1-propanol (127073-84-1) + methylamine (74-89-5) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
In tetrahydrofuran; water at 23℃; for 2h;	99%
In tetrahydrofuran; water at 25℃; for 12h; Inert atmosphere; enantioselective reaction;	98%
In tetrahydrofuran; water at 20℃;	85%

(R)-(3-hydroxy-3-phenylpropyl)carbamic acid ethyl ester (502697-62-3) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Heating;	93%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;	89%

β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
With Rh[((R,R)-BenzP*)(cod)]SbF6; hydrogen; caesium carbonate; zinc(II) chloride In methanol at 20℃; under 19001.3 Torr; for 48h; Autoclave; enantioselective reaction;	93%
Multi-step reaction with 2 steps 1: potassium borohydride / tetrahydrofuran / 66 °C 2: sodium hydrogencarbonate / chloroform; water View Scheme

(1R) 3-phenyl-3-hydroxypropyl methanesulfonate (115290-78-3) + methylamine (74-89-5) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
In tetrahydrofuran; water at 65℃; for 24h;	91%
In tetrahydrofuran; water at 60 - 65℃; for 4h;	80%
In tetrahydrofuran; water at 65℃; for 3h;	837 mg

N-methyl-3-phenylprop-2-en-1-amine (60960-88-5) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Stage #1: N-methyl-3-phenylprop-2-en-1-amine With L-diisopinocampheylborane In 1,2-dimethoxyethane at 30℃; for 2h; Stage #2: With dihydrogen peroxide; potassium hydroxide In 1,2-dimethoxyethane at 20℃; for 2h;	90.67%

(R)-6-phenyl-1,3-oxazinan-2-one R-7a (406218-18-6) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;	90%

(3R)-3-phenyl-3-hydroxypropionic acid methyl amide → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 6h; Reflux;	86%

Phenyl vinyl ketone (768-03-6) + methylamine (74-89-5) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Stage #1: Phenyl vinyl ketone; methylamine With sodium carbonate In water; isopropyl alcohol at 20℃; for 2h; Inert atmosphere; Stage #2: With chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II); sodium formate In water; isopropyl alcohol at 40℃; for 10h; pH=7; Inert atmosphere; enantioselective reaction;	79%

(1R)-3-chloro-1-phenylpropanol (100306-33-0) + methylamine (74-89-5) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
With potassium iodide In methanol; water at 80℃; for 8h;	72%
With sodium iodide In water

3-methylamino-1-phenyl-propan-1-ol; hydrochloride (57256-92-5) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Stage #1: 3-methylamino-1-phenyl-propan-1-ol; hydrochloride With sodium hydrogencarbonate In chloroform; water Stage #2: With (S)-Mandelic acid In acetone	46%

((R)-3-Hydroxy-3-phenyl-propyl)-carbamic acid methyl ester → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;

(R)-3-(N-benzyl-N-methylamino)-1-phenylpropanol hydrochloride → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol for 20h; Ambient temperature; Yield given;

methylamine (74-89-5) + 3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate (51699-49-1) → (S)-N-methyl-3-amino-1-phenyl-1-propanol (114133-37-8) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Stage #1: 3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate With 3 A molecular sieve; oxygen; (-)-sparteine; palladium diacetate In toluene at 80℃; under 760 Torr; for 36h; Stage #2: methylamine With water In tetrahydrofuran at 65℃;

(6R)-2-((S)-1-triisopropylsilyloxyethyl)-3-methyl-6-phenyl-1,3-oxazinane (823182-36-1) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
With hydrogenchloride In methanol; water at 90℃; for 1.5h;

Benzoylacetonitrile (614-16-4) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 74 percent / borane-dimethylsulfide complex; polymer-supported chiral sulfonamide / tetrahydrofuran / Heating 2: sodium hydrogen carbonate / CH2Cl2; H2O / 2 h / 20 °C 3: 93 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating View Scheme

(1R)-3-amino-1-phenyl-1-propanol (138750-31-9) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogen carbonate / CH2Cl2; H2O / 2 h / 20 °C 2: 93 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 88 percent / K2CO3 / CH2Cl2; H2O / 20 °C 2: 89 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme
Multi-step reaction with 2 steps 1: NaHCO3 / tetrahydrofuran 2: LiAlH4 / tetrahydrofuran / Heating View Scheme

butyric acid 2-ethoxycarbonyl-1-phenyl-ethyl ester (118856-08-9) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C 2: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 3: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 4: 80 percent / tetrahydrofuran; H2O / 4 h / 60 - 65 °C View Scheme

Ethyl 3-hydroxy-3-phenylpropanoate (5764-85-2) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: DCC; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C 2: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C 3: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 4: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 5: 80 percent / tetrahydrofuran; H2O / 4 h / 60 - 65 °C View Scheme
Multi-step reaction with 3 steps 1.1: 85 percent / lithium aluminum hydride / tetrahydrofuran / 2 h 2.1: 95 percent / Et3N / CH2Cl2 / 0 h / -10 °C 3.1: O2; (-)-sparteine; 3 Angstroem sieves / Pd(OAc)2 / toluene / 36 h / 80 °C / 760 Torr 3.2: H2O / tetrahydrofuran / 65 °C View Scheme

ethyl (R)-3-hydroxy-3-phenylpropanoate (72656-47-4) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 2: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 3: 80 percent / tetrahydrofuran; H2O / 4 h / 60 - 65 °C View Scheme
Multi-step reaction with 3 steps 1: 86 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 1.5 h / 0 - 20 °C 2: 82 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C 3: 91 percent / tetrahydrofuran; H2O / 24 h / 65 °C View Scheme

(R)-3-phenyl-1,3-dihydroxypropane (103548-16-9) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 2: 80 percent / tetrahydrofuran; H2O / 4 h / 60 - 65 °C View Scheme
Multi-step reaction with 2 steps 1: 82 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C 2: 91 percent / tetrahydrofuran; H2O / 24 h / 65 °C View Scheme
Multi-step reaction with 2 steps 1: 74 percent / triethylamine / diethyl ether / 3 h / -10 - 0 °C 2: 837 mg / H2O; tetrahydrofuran / 3 h / 65 °C View Scheme

benzaldehyde (100-52-7) + SASRIN-maleidobenzoic acid resin → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: tetrahydrofuran; hexane / 1 h / -78 °C 2.1: DCC; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C 3.1: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C 4.1: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 5.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 6.1: 80 percent / tetrahydrofuran; H2O / 4 h / 60 - 65 °C View Scheme

(6R)-2-((S)-1-triisopropylsilyloxyethyl)-6-phenyl-1,3-oxazinan-4-one → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / 20 °C 2: diphenyl silane / tris(triphenylphosphine)rhodium(I) carbonyl hydride / tetrahydrofuran / 15 h / 20 °C 3: HCl / methanol; H2O / 1.5 h / 90 °C View Scheme

(6R)-2-((S)-1-triisopropylsilyloxyethyl)-3-methyl-6-phenyl-1,3-oxazinan-4-one (823182-35-0) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: diphenyl silane / tris(triphenylphosphine)rhodium(I) carbonyl hydride / tetrahydrofuran / 15 h / 20 °C 2: HCl / methanol; H2O / 1.5 h / 90 °C View Scheme

styrene oxide (96-09-3) + 1-chloro-1-phenylethene, 1,2-dichloro-1-phenyl-ethane, benzaldehyde, benzoic acid → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 80 percent / ethanol; H2O / 20 °C 2: 46 percent / Pseudomonas cepacia lipase on modified ceramic particles / diisopropyl ether / 16 h / 27 °C 3: 88 percent / BH3*SMe2 / tetrahydrofuran / Heating 4: 88 percent / K2CO3 / CH2Cl2; H2O / 20 °C 5: 89 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme

3-hydroxy-3-phenylpropanenitrile (73627-97-1, 121617-17-2, 132203-26-0, 17190-29-3) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 46 percent / Pseudomonas cepacia lipase on modified ceramic particles / diisopropyl ether / 16 h / 27 °C 2: 88 percent / BH3*SMe2 / tetrahydrofuran / Heating 3: 88 percent / K2CO3 / CH2Cl2; H2O / 20 °C 4: 89 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme
Multi-step reaction with 3 steps 1: hydrogen, NH3 / Raney Ni / ethanol / 90 °C / p(NH3) = 30 psi and p(H2) = 170 psi 2: NaHCO3 / tetrahydrofuran 3: LiAlH4 / tetrahydrofuran / Heating View Scheme

(R)-3-acetyloxy-3-phenylpropanenitrile (198561-42-1) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / BH3*SMe2 / tetrahydrofuran / Heating 2: 88 percent / K2CO3 / CH2Cl2; H2O / 20 °C 3: 89 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme

ethyl 3-oxo-3-phenylpropionate (94-02-0) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / H2 / RuBr2((S)-(6,6'-(MeO)2-biphenyl-2,2'-diyl)bis(Ph2-phosphane) / ethanol / 18 h / 50 °C / 760.05 Torr 2: 86 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 1.5 h / 0 - 20 °C 3: 82 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C 4: 91 percent / tetrahydrofuran; H2O / 24 h / 65 °C View Scheme

1-phenyl-1,3-propanediol (4850-49-1) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 95 percent / Et3N / CH2Cl2 / 0 h / -10 °C 2.1: O2; (-)-sparteine; 3 Angstroem sieves / Pd(OAc)2 / toluene / 36 h / 80 °C / 760 Torr 2.2: H2O / tetrahydrofuran / 65 °C View Scheme

3-(benzyl methylamino)-1-phenylpropan-1-one hydrochloride (5409-62-1) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2, 2, (2S,4S)-N-(methylcarbamoyl)-4-(dicyclohexylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine / methanol / 48 h / 50 °C / 22800 Torr 2: H2 / 5percent Pd/C / ethanol / 20 h / Ambient temperature View Scheme

acetophenone (98-86-2) + sulfur → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 50 percent / concd. HCl / ethanol / 4 h / Heating 2: H2, 2, (2S,4S)-N-(methylcarbamoyl)-4-(dicyclohexylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine / methanol / 48 h / 50 °C / 22800 Torr 3: H2 / 5percent Pd/C / ethanol / 20 h / Ambient temperature View Scheme

ortho-methylphenyl iodide (615-37-2) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) → atomoxetine hydrochloride (82248-59-7)

Conditions	Yield
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium carbonate; copper(l) iodide In toluene at 148℃; for 21h; Ullmann type reaction; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With sodium hydroxide In water pH=11 - 12;	99%
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium carbonate; copper(l) iodide In toluene at 148℃; for 21h; Ullmann type reaction; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With sodium hydroxide In water pH=11 - 12;	94%
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium phosphate; copper(l) iodide In toluene for 24h; Ullmann type reaction; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With sodium hydroxide In water pH=12 - 14;	82%

4-chlorobenzotrifluoride (98-56-6) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) → (R)-fluoxetine (54910-89-3, 57226-07-0, 100568-02-3, 100568-03-4)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 80 - 90℃; for 1h;	92%
In N,N-dimethyl acetamide	86%
In N,N-dimethyl acetamide	86%

2-Fluorotoluene (95-52-3) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) → (R)-tomoxetine (105314-52-1, 105314-53-2, 63940-51-2, 83015-26-3)

Conditions	Yield
Stage #1: (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium hydroxide In dimethyl sulfoxide at 130℃; for 1h; Stage #2: 2-Fluorotoluene In dimethyl sulfoxide at 130℃;	89.51%
Stage #1: (R)-N-methyl-3-phenyl-3-hydroxypropylamine With sodium hydride In dimethyl sulfoxide for 0.25h; Stage #2: With Potassium benzoate In dimethyl sulfoxide at 50 - 55℃; for 1h; Stage #3: 2-Fluorotoluene In dimethyl sulfoxide at 50 - 120℃; for 6.25 - 7.25h;
With potassium tert-butylate In dimethyl sulfoxide at 60℃; for 8h;

4-Fluorobenzotrifluoride (402-44-8) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) → (R)-fluoxetine (54910-89-3, 57226-07-0, 100568-02-3, 100568-03-4)

Conditions	Yield
Stage #1: (R)-N-methyl-3-phenyl-3-hydroxypropylamine With sodium hydride In N,N-dimethyl acetamide; paraffin oil at 90℃; for 0.5h; Inert atmosphere; Stage #2: 4-Fluorobenzotrifluoride In N,N-dimethyl acetamide; paraffin oil at 100℃; for 5h; Inert atmosphere;	88%

(R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) + C7H7X → atomoxetine hydrochloride (82248-59-7)

Conditions	Yield
Stage #1: (R)-N-methyl-3-phenyl-3-hydroxypropylamine; C7H7X In ethyl acetate at 77℃; Stage #2: With hydrogenchloride In water; acetone pH=1 - 2;	73%

2-Fluorotoluene (95-52-3) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) → rac-tomoxetine hydrochloride

Conditions	Yield
With sodium hydride 1) DMSO, 2) DMSO; Yield given. Multistep reaction;

2-methylchlorobenzene (95-49-8) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) → (R)-tomoxetine (105314-52-1, 105314-53-2, 63940-51-2, 83015-26-3)

Conditions	Yield
With 2,4-dichlorophenoxyacetic acid dimethylamine; sodium hydride Multistep reaction;

2-Chloroanisole (766-51-8) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) → (R)-3-(2-methoxyphenoxy)-N-methyl-3-phenylpropan-1-amine (112066-67-8)

Conditions	Yield
With 2,4-dichlorophenoxyacetic acid dimethylamine; sodium hydride Multistep reaction;

ortho-cresol (95-48-7) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) → atomoxetine hydrochloride (82248-59-7)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate Yield given. Multistep reaction;

4-chlorobenzotrifluoride (98-56-6) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) → (R)-fluoxetine hydrochloride (114247-09-5)

Conditions	Yield
With sodium hydride 1) DMSO, 50 deg C, 20 min, 2) DMSO, 90 deg C, 40 min; Yield given. Multistep reaction;
With sodium hydride 1.) N,N-dimethylacetamide, a) 0 deg C, 5 min, b) 70 deg C, 30 min, 2.) N,N-dimethylacetamide, 100 deg C, 3 h; Yield given. Multistep reaction;
With sodium hydride 1,) 0 deg C, then 70 deg C, 30 min; 2.) 2.5 h, 100 deg C; Yield given. Multistep reaction;

Upstream product

• 74-89-5 methylamine 
• 51699-49-1 3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate 
• 5764-85-2 Ethyl 3-hydroxy-3-phenylpropanoate 
• 198561-42-1 (R)-3-acetyloxy-3-phenylpropanenitrile 
• 100-52-7 benzaldehyde 
• 103548-16-9 (R)-3-phenyl-1,3-dihydroxypropane 
• 72656-47-4 ethyl (R)-3-hydroxy-3-phenylpropanoate 
• 118856-08-9 butyric acid 2-ethoxycarbonyl-1-phenyl-ethyl ester 
• 138750-31-9 (1R)-3-amino-1-phenyl-1-propanol 
• 614-16-4 Benzoylacetonitrile 
• 823182-36-1 (6R)-2-((S)-1-triisopropylsilyloxyethyl)-3-methyl-6-phenyl-1,3-oxazinane 
• 502697-62-3 (R)-(3-hydroxy-3-phenylpropyl)carbamic acid ethyl ester 
• 406218-18-6 (R)-6-phenyl-1,3-oxazinan-2-one R-7a 
• 115290-78-3 (1R) 3-phenyl-3-hydroxypropyl methanesulfonate 

Downstream Products

• 82857-40-7 rac-tomoxetine hydrochloride 
• 105314-52-1 (R)-tomoxetine 
• 54910-89-3 (R)-fluoxetine 
• 1620141-91-4 (R)-N-methyl-N-{3-phenyl-3-[4-trifluoromethyl]phenoxylpropyl}acetamide 
• 82248-59-7 atomoxetine hydrochloride 
• 1351468-93-3 (R)-N-(3-hydroxy-3-phenylpropyl)-N-methylacetamide 
• 114247-09-5 (R)-fluoxetine hydrochloride 
• 112066-67-8 (R)-N-methyl-3-(2-methoxyphenoxy)-3-phenyl-1-propanamine 

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