(S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one supplier

Name
3-MORPHOLINONE, 4-[4-[(5S)-5-(AMINOMETHYL)-2-OXO-3-OXAZOLIDINYL]PHENYL]-
EINECS 692-970-2
CAS No. 446292-10-0
Article Data39
CAS DataBase
Density 1.348 g/cm³
Solubility
Melting Point 148.3-149.8 °C
Formula C₁₄H₁₇N₃O₄
Boiling Point 580.4 °C at 760 mmHg
Molecular Weight 291.307
Flash Point 304.8 °C
Transport Information
Appearance White solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one;
PSA 85.10000
LogP 1.16400

Synthetic route

: 1372665-04-7
4-{4-[(5S)-5-((dibenzylamino)methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 40 - 50℃; under 37503.8 Torr; for 20h; Solvent; Reagent/catalyst;	100%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 50℃; for 18h; Inert atmosphere;	92.6%
With palladium 10% on activated carbon; hydrogen; acetic acid In methanol at 50℃; under 4200.42 Torr;	2.56 g

: 1414932-72-1
4-{4-[(S)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
With isobutylamine In toluene for 3h; Product distribution / selectivity; Reflux;	99.7%
With isobutylamine In toluene for 3h; Concentration; Solvent; Time; Temperature; Reagent/catalyst; Heating; Reflux;	99.7%
With hydrogenchloride; triethylamine In ethanol; water at 22 - 65℃; for 1h;	95%
With hydrogenchloride In water for 0.333333h; Time;

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
In dichloromethane; water pH=8; Concentration;	96.7%
With potassium carbonate In methanol at 25 - 30℃; for 0.5h;	56%
With potassium carbonate In methanol at 25 - 30℃; for 0.5h;	56%
With potassium carbonate In water at 20℃; for 2h;

: 446292-08-6
2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
With hydrazine hydrate In methanol at 80℃; for 2.5h;	96.1%
With ethanolamine In toluene at 75 - 85℃; for 2h; Solvent; Temperature;	95.87%
With hydrazine hydrate In ethanol for 2h; Reflux;	95.4%

: 1349248-79-8
4-{4-[(5R)-5-(azidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol at 40℃; for 24h;	96%
With 5%-palladium/activated carbon; hydrogen In ethyl acetate for 12h;	91%
With palladium 10% on activated carbon; hydrogen In methanol under 1500.15 - 3000.3 Torr; for 4h;	90.9%
With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 45℃; under 3750.38 - 6000.6 Torr; for 8h; Autoclave;	80%
With water; triphenylphosphine In tetrahydrofuran at 10 - 65℃;	18 g

: 446292-07-5
2-((2R)-2-hydroxy-3-{[4-(3-oxo-4-morpholinyl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione

: 74-89-5
methylamine

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Stage #1: 2-((2S)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione With dmap; 1,1'-carbonyldiimidazole In tetrahydrofuran for 12h; Reflux; Stage #2: methylamine In ethanol; water for 8h; Reflux;	92.2%

: 1416129-92-4
tert-butyl {(5S)-3-[4-(3-oxo-4-morpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methylcarbamate

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
With hydrogenchloride; water In ethanol at 20℃; for 24h; Solvent;	90%
With hydrogenchloride In ethanol; water at 20℃; for 24h; Solvent;	90%

: 1414932-73-2
(S)-4-(4-{5-[(benzylidene-amino)-methyl]-2-oxo-oxazolidine-3-yl}-phenyl)-morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
With hydrogenchloride; water In ethanol at 20℃; for 24h; Solvent;	90%
With hydrogenchloride In ethanol; water at 20℃; for 24h; Solvent; Time;	90%

: C14H14N2O5

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Stage #1: C14H14N2O5 With ammonium hydroxide In methanol for 0.5h; Stage #2: With methanol; sodium tetrahydroborate at 0 - 20℃; for 2.5h;	87.5%

: 446292-08-6
2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione

: 74-89-5
methylamine

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
In methanol; water for 2h; Reflux;	85%

: 446292-08-6
2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione

A: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

B: 1445-69-8
2,3-dihydrophthalazine-1,4-dione

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol at 65℃; for 3h;	A 73% B 12.7%

: 446292-07-5
2-((2R)-2-hydroxy-3-{[4-(3-oxo-4-morpholinyl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 24 h / 60 °C 2: aq. MeNH2 / ethanol / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: toluene / 3 h / Industry scale; Reflux 2.1: methylamine / ethanol / 4 h / 65 °C / Industry scale 2.2: 58 - 60 °C / pH 2.7 / Industry scale View Scheme
Multi-step reaction with 2 steps 1: dichloromethane / 20 h / 30 °C 2: hydrazine hydrate / methanol / 1 h / Reflux View Scheme

: 438056-69-0
4-(4-aminophenyl)morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / ethanol; H2O / 27 h / Heating 2: 87 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 24 h / 60 °C 3: aq. MeNH2 / ethanol / 1 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: water / ethanol / 36 h / 60 °C / Industry scale 2.1: toluene / 3 h / Industry scale; Reflux 3.1: methylamine / ethanol / 4 h / 65 °C / Industry scale 3.2: 58 - 60 °C / pH 2.7 / Industry scale View Scheme
Multi-step reaction with 4 steps 1: toluene / 20 °C / Reflux 2: MgI2*etherate / tetrahydrofuran / 20 - 80 °C / Inert atmosphere 3: sodium azide / N,N-dimethyl-formamide / 12 h / 85 °C 4: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 12 h View Scheme

: 122-98-5
2-Anilinoethanol

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: sodium hydroxide / ethanol; water / 0.5 h / 38 - 45 °C / pH 10 - 13 / Industry scale 2.1: nitric acid; sulfuric acid / sulfolane / 2 h / -5 - 30 °C 3.1: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C 4.1: water / ethanol / 36 h / 60 °C / Industry scale 5.1: toluene / 3 h / Industry scale; Reflux 6.1: methylamine / ethanol / 4 h / 65 °C / Industry scale 6.2: 58 - 60 °C / pH 2.7 / Industry scale View Scheme
Multi-step reaction with 7 steps 1: sodium hydroxide / ethanol; water 2: sulfuric acid; nitric acid / water 3: 5%-palladium/activated carbon; hydrogen / ethanol / 40 °C 4: toluene / 20 °C / Reflux 5: MgI2*etherate / tetrahydrofuran / 20 - 80 °C / Inert atmosphere 6: sodium azide / N,N-dimethyl-formamide / 12 h / 85 °C 7: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 12 h View Scheme

Yield

Multi-step reaction with 6 steps
1.1: sodium hydroxide / ethanol; water / 0.5 h / 38 - 45 °C / pH 10 - 13 / Industry scale
2.1: nitric acid; sulfuric acid / sulfolane / 2 h / -5 - 30 °C
3.1: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C
4.1: water / ethanol / 36 h / 60 °C / Industry scale
5.1: toluene / 3 h / Industry scale; Reflux
6.1: methylamine / ethanol / 4 h / 65 °C / Industry scale
6.2: 58 - 60 °C / pH 2.7 / Industry scale
View Scheme

Multi-step reaction with 7 steps
1: sodium hydroxide / ethanol; water
2: sulfuric acid; nitric acid / water
3: 5%-palladium/activated carbon; hydrogen / ethanol / 40 °C
4: toluene / 20 °C / Reflux
5: MgI2*etherate / tetrahydrofuran / 20 - 80 °C / Inert atmosphere
6: sodium azide / N,N-dimethyl-formamide / 12 h / 85 °C
7: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 12 h
View Scheme

: 446292-04-2
4-(4-nitrophenyl)-3-morpholinone

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C 2.1: water / ethanol / 36 h / 60 °C / Industry scale 3.1: toluene / 3 h / Industry scale; Reflux 4.1: methylamine / ethanol / 4 h / 65 °C / Industry scale 4.2: 58 - 60 °C / pH 2.7 / Industry scale View Scheme
Multi-step reaction with 5 steps 1: 5%-palladium/activated carbon; hydrogen / ethanol / 40 °C 2: toluene / 20 °C / Reflux 3: MgI2*etherate / tetrahydrofuran / 20 - 80 °C / Inert atmosphere 4: sodium azide / N,N-dimethyl-formamide / 12 h / 85 °C 5: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 12 h View Scheme
Multi-step reaction with 4 steps 1: ammonium formate / water / 30 - 90 °C 2: water / 8 h / 80 °C 3: dmap / 6 h / 80 - 85 °C 4: methylamine / water / 5 h / 35 °C View Scheme

: 29518-11-4
4-phenyl-3-morpholinone

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: nitric acid; sulfuric acid / sulfolane / 2 h / -5 - 30 °C 2.1: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C 3.1: water / ethanol / 36 h / 60 °C / Industry scale 4.1: toluene / 3 h / Industry scale; Reflux 5.1: methylamine / ethanol / 4 h / 65 °C / Industry scale 5.2: 58 - 60 °C / pH 2.7 / Industry scale View Scheme
Multi-step reaction with 6 steps 1: sulfuric acid; nitric acid / water 2: 5%-palladium/activated carbon; hydrogen / ethanol / 40 °C 3: toluene / 20 °C / Reflux 4: MgI2*etherate / tetrahydrofuran / 20 - 80 °C / Inert atmosphere 5: sodium azide / N,N-dimethyl-formamide / 12 h / 85 °C 6: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 12 h View Scheme

: 1252018-28-2
4-{4-[(5R)-5-(chloromethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 12 h / 85 °C 2: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 12 h View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 5 h / Reflux 2: hydrazine hydrate / methanol / 1 h / Reflux View Scheme

: 1325210-64-7
4-(4-isocyanatophenyl)morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: MgI2*etherate / tetrahydrofuran / 20 - 80 °C / Inert atmosphere 2: sodium azide / N,N-dimethyl-formamide / 12 h / 85 °C 3: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 12 h View Scheme
Multi-step reaction with 2 steps 1: lithium bromide; Triphenylphosphine oxide / 1-methyl-pyrrolidin-2-one / 7 h / 90 - 95 °C 2: potassium hydroxide / water / Reflux View Scheme

: 1252018-10-2
4-[4-(N-(3-chloro-(2R)-2-hydroxy-1-propyl)amino)phenyl]morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dichloromethane / 20 h / 30 °C 2: N,N-dimethyl-formamide / 5 h / Reflux 3: hydrazine hydrate / methanol / 1 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: chloroform / 20 h / 30 °C 2: N,N-dimethyl-formamide / 5 h / Reflux 3: hydrazine hydrate / methanol / 1 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 5 h / Reflux 2: dichloromethane / 20 h / 30 °C 3: hydrazine hydrate / methanol / 1 h / Reflux View Scheme

: 1313613-18-1
[4-(3-oxo-morpholin-4-yl)phenyl]carbamic acid benzyl ester

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium tert-butoxide / dichloromethane / 24 h / Reflux 2: isobutylamine / toluene / 3 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: lithium tert-butoxide; methanol / tetrahydrofuran; N,N-dimethyl-formamide / 0.17 h / 0 °C 1.2: 18 h / 30 °C 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: lithium tert-butoxide; methanol / tetrahydrofuran; N,N-dimethyl-formamide / 0.17 h / 0 °C 1.2: 18 h / 30 °C 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C 4.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr View Scheme

: 1414932-71-0
dodecyl (4-(3-oxomorpholin)phenyl)carbamate

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium tert-butoxide / dichloromethane / 36 h / Reflux 2: isobutylamine / toluene / 3 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: n-butyllithium / dichloromethane / 36 h / Heating; Reflux 2: isobutylamine / toluene / 3 h / Heating; Reflux View Scheme

: 1424942-78-8
4-{4-[(5S)-5-(N-benzylaminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morphoIin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen; acetic acid In methanol at 45℃; under 3750.38 - 6000.6 Torr; for 8h; Autoclave;	15.5 g

: 1447919-65-4
4-[4-{(R)-2,3-dihydroxy-propylamino}phenyl]morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: methanol / 48 h / 30 °C 1.2: 2 h / Reflux 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: methanol / 48 h / 30 °C 1.2: 2 h / Reflux 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C 4.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr View Scheme
Multi-step reaction with 4 steps 1: triethylamine / chloroform / 1 h / -5 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 10 h / 80 °C 3: sodium azide / water; N,N-dimethyl-formamide / 10 h / 0 - 40 °C 4: 5%-palladium/activated carbon; hydrogen / ethanol / 24 h / 40 °C View Scheme

: 1446022-14-5
butyric acid-2(R)-2-hydroxy-3-[4-(3-oxo-morpholin-4-yl)phenylamino]-propyl ester

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: methanol / 48 h / 30 °C 1.2: 2 h / Reflux 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: methanol / 48 h / 30 °C 1.2: 2 h / Reflux 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C 4.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr View Scheme
Multi-step reaction with 5 steps 1: dichloromethane / 48 h / 30 °C 2: sodium methylate; methanol / 1 h / 30 °C 3: triethylamine / dichloromethane / 18 h / 0 - 20 °C 4: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 5: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1: dichloromethane / 48 h / 30 °C 2: sodium methylate; methanol / 1 h / 30 °C 3: triethylamine / dichloromethane / 18 h / 0 - 20 °C 4: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C 5: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr View Scheme

: 1446022-15-6
butyric acid-2-oxo-5(R)-3-[4-(3-oxomorpholin-4-yl)-phenyl]oxazolidin-5-yl-methyl ester

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium methylate; methanol / 1 h / 30 °C 2: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: sodium methylate; methanol / 1 h / 30 °C 2: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C 4: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr View Scheme

: 1117893-59-0
4-(4-((R)-5-benzyloxymethyl-2-oxo-oxazolidin-3-yl)phenyl)morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave 2: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave 2: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C 4: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr View Scheme

: 1117893-58-9
4-(4-(R)-3-benzyloxy-2-hydroxy-propylamino)phenyl-morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: dichloromethane / 44 h / 30 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave 3: triethylamine / dichloromethane / 18 h / 0 - 20 °C 4: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 5: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1: dichloromethane / 44 h / 30 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave 3: triethylamine / dichloromethane / 18 h / 0 - 20 °C 4: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C 5: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr View Scheme

: 1447919-68-7
acetic acid-1-benzyloxymethyl-2-[(R)-4-(3-oxo-morpholin-4-yl)phenylamino]-ethylester

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: chloroform / 2 h / 50 °C 2: lithium tert-butoxide; methanol / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 °C 3: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave 4: triethylamine / dichloromethane / 18 h / 0 - 20 °C 5: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 6: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 6 steps 1: chloroform / 2 h / 50 °C 2: lithium tert-butoxide; methanol / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 °C 3: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave 4: triethylamine / dichloromethane / 18 h / 0 - 20 °C 5: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C 6: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr View Scheme

Yield

Multi-step reaction with 6 steps
1: chloroform / 2 h / 50 °C
2: lithium tert-butoxide; methanol / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 °C
3: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave
4: triethylamine / dichloromethane / 18 h / 0 - 20 °C
5: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
6: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere
View Scheme

Multi-step reaction with 6 steps
1: chloroform / 2 h / 50 °C
2: lithium tert-butoxide; methanol / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 °C
3: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave
4: triethylamine / dichloromethane / 18 h / 0 - 20 °C
5: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C
6: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr
View Scheme

: 1447919-69-8
acetic acid-1-benzyloxymethyl-2-{[(R)-(3-oxo-morpholin-4-yl)-phenyl]-chlorocarbonyl-amino} ethyl ester

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: lithium tert-butoxide; methanol / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave 3: triethylamine / dichloromethane / 18 h / 0 - 20 °C 4: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 5: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1: lithium tert-butoxide; methanol / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave 3: triethylamine / dichloromethane / 18 h / 0 - 20 °C 4: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C 5: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr View Scheme

Yield

Multi-step reaction with 5 steps
1: lithium tert-butoxide; methanol / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 °C
2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave
3: triethylamine / dichloromethane / 18 h / 0 - 20 °C
4: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C
5: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere
View Scheme

Multi-step reaction with 5 steps
1: lithium tert-butoxide; methanol / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 °C
2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3000.3 - 3750.38 Torr / Autoclave
3: triethylamine / dichloromethane / 18 h / 0 - 20 °C
4: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C
5: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr
View Scheme

: 1447919-71-2
4-(4-((R)-5-((phenyloxycarbonyloxy)methyl)-2-oxo-oxazolidin-3-yl)phenyl)-morpholin-3-one

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium methylate; methanol / 4 h / 30 °C 2: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3: sodium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C 4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: sodium methylate; methanol / 4 h / 30 °C 2: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C 4: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 1500.15 - 3000.3 Torr View Scheme

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 42518-98-9
5-chlorothiophene-2-carbonyl chloride

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 3h; Product distribution / selectivity;	100%
With triethylamine In tetrahydrofuran at 20℃; for 3h; Reagent/catalyst; Solvent; Time; Concentration; Temperature;	100%
With sodium carbonate In water; acetone; toluene at 8 - 53℃; for 0.5h;	98.7%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 64-18-6
formic acid

: 1616563-62-2
N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)formamide

Conditions

Conditions	Yield
In toluene at 110 - 120℃; Solvent;	96%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 5271-67-0
2-Thiophenecarbonyl chloride

: N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide

Conditions

Conditions	Yield
With 4-methyl-morpholine In water; acetonitrile at -5 - 20℃; for 2.5h; Reagent/catalyst;	96%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 24065-33-6
5-Chlorothiophene-2-carboxylic acid

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With 4-methyl-morpholine; hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 2.83333h;	95.2%
With ortho-iodophenylboronic acid In dichloromethane at 30℃; for 48h; Reagent/catalyst; Time; Concentration; Temperature; Solvent; Dean-Stark;	85%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;	68.9%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 39608-31-6
N-(Benzyloxycarbonyl)sarcosine

: 947181-22-8
C25H28N4O7

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;	92%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: C11H6ClN3O2S

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With triethylamine at 10 - 25℃;	90.3%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 122-01-0
4-chloro-benzoyl chloride

: 4-chloro-N-{2-oxo-3-[4-(3-oxo-morpholin-4-yl)-phenyl]-oxazolidin-5-ylmethyl}-benzamide

Conditions

Conditions	Yield
With pyridine; aminomethylpolystyrol resin at 20℃; for 3.5h;	89%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 5538-51-2
O-acetylsalicyloyl chloride

: C23H23N3O7

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	73%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 6843-36-3
2-(methylcarbamoyl)benzoic acid.

: (S)-N1-methyl-N2-((2-oxo-3-(4-(3-oxomorpholin-4-yl)phenyl)oxazolidin-5-yl)methyl)phthalamide

Conditions

Conditions	Yield
Stage #1: 2-(methylcarbamoyl)benzoic acid. With sodium hydrogencarbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: With isobutyl chloroformate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #3: 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one In N,N-dimethyl-formamide for 8h;	65%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 1365267-37-3
(S)-2-(((2-oxo-3-(4-(3-oxomorpholin-4-yl)phenyl)oxazolidin-5-yl)methyl)carbamoyl)benzoic acid

: 1365267-36-2
N,N'-bis[{(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl]benzene-1,2-diamide

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; acetonitrile at 5℃; for 2.16667h; pH=8;	62.8%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 1450877-56-1
4-nitrophenyl 5-chlorothiophene-2-carboxylate

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane at 25 - 30℃;	55.5%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 2-[2-({4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}amino)ethoxy]acetohydrazide

Conditions

Conditions	Yield
With hydrazine hydrate In methanol at 80℃; for 12h; Temperature; Solvent;	49.5%
With hydrazine hydrate In methanol at 80℃; for 12h;	49.5%
With hydrazine hydrate In methanol at 90℃; for 12h;	49.5%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 527-72-0
2-thiophenylcarboxylic acid

: N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 2-thiophenylcarboxylic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one In dichloromethane at 20℃; for 6h; Inert atmosphere;	48%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: (S)-4-(4-(((2-oxooxazolidin-5-yl)methyl)amino)phenyl)morpholin-3-one

Conditions

Conditions	Yield
In water at 130℃; for 12h; Temperature; Time; Solvent; Autoclave;	46%
With water at 130℃; for 12h; Sealed tube;	46%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 2766-74-7
5-chlorothien-2-ylsulfonyl chloride

: 5-Chloro-thiophene-2-sulfonic acid {(R)-2-oxo-3-[4-(3-oxo-morpholin-4-yl)-phenyl]-oxazolidin-5-ylmethyl}-amide

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 4h;	43%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 32315-10-9
bis(trichloromethyl) carbonate

: 1365267-35-1
N,N'-bis[{(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl]urea

Conditions

Conditions	Yield
Stage #1: 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one; bis(trichloromethyl) carbonate With triethylamine In tetrahydrofuran at 20℃; Cooling; Stage #2: With sodium carbonate In tetrahydrofuran	38.8%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 7311-63-9
5-bromothiophene-2-carboxylic acid

: 5-bromo-N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 5-bromothiophene-2-carboxylic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one In dichloromethane at 20℃; for 6h; Inert atmosphere;	37%
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: (5-fluorothiophen-2-yl)formyl chloride

: (S)-5-fluoro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)thiophene-2-carboxamide

Conditions

Conditions	Yield
With pyridine at 0 - 23℃; for 1h; Inert atmosphere;	37%

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 4684-94-0
6-chloropicolinic acid

: 6-chloro-N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)pyridine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 6-chloropicolinic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one In dichloromethane at 20℃; for 6h; Inert atmosphere;	27%

(S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one Specification

The 3-Morpholinone,4-[4-[(5S)-5-(aminomethyl)-2-oxo-3-oxazolidinyl]phenyl]-, with the CAS registry number 446292-10-0, is also known as (S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one. This chemical's molecular formula is C₁₄H₁₇N₃O₄ and molecular weight is 291.30. Its systematic name is called 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one.

Physical properties of 3-Morpholinone,4-[4-[(5S)-5-(aminomethyl)-2-oxo-3-oxazolidinyl]phenyl]-: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 7; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 4; (8)Index of Refraction: 1.598; (9)Molar Refractivity: 73.75 cm³; (10)Molar Volume: 216 cm³; (11)Surface Tension: 57.4 dyne/cm; (12)Density: 1.348 g/cm³; (13)Flash Point: 304.8 °C; (14)Enthalpy of Vaporization: 86.82 kJ/mol; (15)Boiling Point: 580.4 °C at 760 mmHg; (16)Vapour Pressure: 1.83E-13 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1O[C@@H](CN)CN1c3ccc(N2C(=O)COCC2)cc3
(2)InChI: InChI=1/C14H17N3O4/c15-7-12-8-17(14(19)21-12)11-3-1-10(2-4-11)16-5-6-20-9-13(16)18/h1-4,12H,5-9,15H2/t12-/m0/s1
(3)InChIKey: DEXXSYVEWAYIGZ-LBPRGKRZBF

Product Name

3-MORPHOLINONE, 4-[4-[(5S)-5-(AMINOMETHYL)-2-OXO-3-OXAZOLIDINYL]PHENYL]-

Synthetic route

(S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one Specification

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