90719-32-7

Basic information

• Product Name: (S)-4-Benzyl-2-oxazolidinone
• Synonyms: (4S)-4-BENZYL-1,3-OXAZOLIDIN-2-ONE;4-S-BENZYL-OXAZOLIDIN-2-ONE;2-OXAZOLIDINONE, 4-(PHENYLMETHYL)-, (4S)-;(S)-(-)-4-BENZYL-2-OXAZOLIDINONE;(S)-4-BENZYL-2-OXAZOLIDINONE;(S)-(-)-4-BENZYL-2-OXAZOLIDONE;(S)-4-BENZYL-OXAZOLIDIN-2-ONE;S(-)-4-BENZYLOXAZOLIDIN-2-ONE
• CAS NO: 90719-32-7
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• EINECS: 1592732-453-0
• Product Categories: Oxazolidinone;Chiral Compounds;chiral;Aromatics Compounds;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Chiral chemicals;Peptide;Aromatics;Chiral Reagents;Heterocycles;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives;aliskiren
• Mol File: 90719-32-7.mol
• Article Data: 183

Chemical Properties

• Melting Point: 86-88 °C(lit.)
• Boiling Point: 309.12°C (rough estimate)
• Flash Point: 195 °C
• Appearance: White to very slightly yellow/Crystalline Powder
• Density: 1.1607 (rough estimate)
• Refractive Index: -14.5 ° (C=5, MeOH)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.78±0.40(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Hygroscopic
• BRN: 3649667
• CAS DataBase Reference: (S)-4-Benzyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Benzyl-2-oxazolidinone(90719-32-7)
• EPA Substance Registry System: (S)-4-Benzyl-2-oxazolidinone(90719-32-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26-37/39
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 90719-32-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 90719-32-7 differently. You can refer to the following data:
1. (S)-(-)-4-Benzyl-2-oxazolidinone is used in chiral auxiliary asymmetric alkylation. It has been used in the synthesis of (S)-equol. Preparation and functionalization of chiral, stabilized ylides. It was used for asymmetric synthesis of (3R)- and (3S)-piperazic acid.
2. As an oxazolidinone, (S)-4-Benzyl-2-Oxazolidinone can be used in chiral auxiliary asymetric synthesis.

Synthetic route

L-Phenylalaninol (3182-95-4) + Diethyl carbonate (105-58-8) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With potassium carbonate In ethyl acetate at 120 - 130℃; for 3h;	100%
With potassium carbonate In ethanol at 130 - 135℃; for 1h;	88%
With potassium carbonate at 135 - 140℃; for 2h;	84%

(4S,3'R)-3-[3'-(N,N-dibenzylamino)-3'-phenylpropanoyl]-4-benzyloxazolidin-2-one (717137-43-4) → (R)-3-phenyl-3-aminopropionic acid (614-19-7, 3646-50-2, 13921-90-9, 40856-44-8) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
Stage #1: (4S,3'R)-3-[3'-(N,N-dibenzylamino)-3'-phenylpropanoyl]-4-benzyloxazolidin-2-one With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 16h; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With Pearlman's catalist; hydrogen In methanol at 20℃; for 24h;	A 43% B 100%

(S)-3-((2S,4S)-2-Azido-4-methyl-hexanoyl)-4-benzyl-oxazolidin-2-one (213385-64-9) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7) + (2S,4S)-2-Azido-4-methyl-hexanoic acid (221292-86-0)

Conditions	Yield
Stage #1: (S)-3-((2S,4S)-2-Azido-4-methyl-hexanoyl)-4-benzyl-oxazolidin-2-one With lithium hydroxide In tetrahydrofuran; water at 0℃; for 1h; Stage #2: With hydrogenchloride In water pH=1 - 2;	A 99% B 96.7%

methanol (67-56-1) + (4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone (181431-20-9) → methyl (2R)-2-methyl-3-phenylpropanoate (29393-16-6) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃; for 72h;	A 98% B 99%

ethanol (64-17-5) + (4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone (198649-20-6) → ethyl laurate (106-33-2) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃; for 168h;	A 99% B 99%

(4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone (198649-20-6) + benzyl alcohol (100-51-6) → benzyl dodecanoate (140-25-0) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃; for 168h;	A 83% B 99%

(S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5, 101711-78-8) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With methanol; C17H23BN2O at 25℃; under 760.051 Torr; for 1h; Inert atmosphere; chemoselective reaction;	98%
Multi-step reaction with 2 steps 1: 1.) di-n-butylboron triflate, N,N-diisopropylethylamine, 3.) aq. H2O2 / 1) CH2Cl2, 0 deg C, 30 min; 2) CH2Cl2, -78 deg C, 45 min, 0 deg C, 2 h; 3) methanol, 0 deg C, 1 h 2: 1.) trimethylaluminum / 1) CH2Cl2, toluene, rt, 1 h; 2) CH2Cl2, toluene, -20 deg C --> rt, rt, 1.5 h View Scheme
Multi-step reaction with 2 steps 1: 1.) dibutylboron trifluoromethanesulfonate, diisopropylethylamine / 1.) CH2Cl2, 0 deg C, 1 h, 2.) CH2Cl2, -78 deg C (1 h), room temp. (5 h) 2: 80 percent / LiBH4, H2O / tetrahydrofuran / 3 h / Ambient temperature View Scheme

(S)-4-benzyl-3-((1'R,2'S,3'R,7a'R)-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-ylcarbonyl)oxazolidin-2-one + carbonic acid dimethyl ester (616-38-6) → methyl (1'R,2'S,7a'R,11R)-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylate + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With sodium methylate In dichloromethane at 20℃; for 4h;	A 98% B 96%

N-(4-benzyl-2-oxo-oxazolidin-3-yl)-N-(5-chloro-1-propyl-pentyl)-benzamide (373363-70-3) → N-(5-chloro-1-propyl-pentyl)-benzamide (373363-71-4) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran for 0.166667h;	A 97% B n/a

tert-butyl (3R)-4-[(S)-4-benzyl-2-oxooxazolidin-3-yl]-3-[3-(benzyloxy)benzyl]-4-oxobutanoate (1352791-77-5) → (3R)-2-[3-(benzyloxy)benzyl]-4-tert-butoxy-4-oxobutanoic acid (1352791-75-3) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water for 3h;	A 97% B 89%

(S)-4-benzyl-3-((1'S,2'S,3'R,7a'R)-1'-methyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-ylcarbonyl)oxazolidin-2-one + carbonic acid dimethyl ester (616-38-6) → methyl (1'S,2'S,7a'R,11R)-1'-methyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylate + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With sodium methylate In dichloromethane at 20℃; for 4h;	A 97% B n/a

(S)-4-benzyl-3-((1'R,2'S,3'R,7a'R)-7,8-dimethyl-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-ylcarbonyl)oxazolidin-2-one + carbonic acid dimethyl ester (616-38-6) → methyl (1'R,2'S,7a'R,11R)-7,8-dimethyl-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylate + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With sodium methylate In dichloromethane at 20℃; for 4h;	A 97% B n/a

(4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone (181431-20-9) → 2-methyl-3-phenylpropionic acid (14367-67-0) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
Stage #1: (4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone With ytterbium(III) triflate In methanol for 3h; Stage #2: With lithium hydroxide In tetrahydrofuran; water for 2h;	A 97% B 97%

(S)-ethyl (1-hydroxy-3-phenylpropan-2-yl)carbamate (161646-29-3) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With potassium carbonate In toluene for 3h; Heating;	96%
With potassium carbonate at 100 - 130℃;
With hydrotalcite; magnesium aluminum In toluene at 110℃; for 5h;	91 % Spectr.
With potassium carbonate at 125 - 130℃; under 33.7534 - 37.5038 Torr;
With polyethylene glycol 400(PEG-400) In toluene Reflux; Large scale;	167 kg

(4S)-3-<(2S,3S)-3-hydroxy-2-methyl-1-oxo-3-(1-phenylsulfanylcyclopentyl)propyl>-4-phenylmethyl-1,3-oxazolidin-2-one (138649-96-4) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7) + (1S,2S)-2-methyl-1-(1-phenylsulfanylcyclopentyl)propane-1,3-diol (138751-07-2)

Conditions	Yield
With lithium borohydride; water In tetrahydrofuran for 3h; Ambient temperature;	A 80% B 96%

carbon monoxide (201230-82-2) + L-Phenylalaninol (3182-95-4) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With sodium acetate; palladium diacetate In acetonitrile at 20℃; under 760 Torr; Electrolysis;	96%
With copper diacetate; air; palladium diacetate In toluene under 760 Torr; for 2h; Heating;	88%
With oxygen; copper-(N-heterocyclic carbene) complex In 1,4-dioxane at 100℃; under 37503.8 Torr; for 3h;	86%

ethyl 1-imidazolecarboxylate (19213-72-0) + L-Phenylalaninol (3182-95-4) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 15h; Reflux;	96%

(S)-4-benzyl-3-((2'R,3'S,4'R)-1'-methyl-4'-phenylspiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidine]-3'-ylcarbonyl)oxazolidin-2-one + carbonic acid dimethyl ester (616-38-6) → methyl (3'S,4'R,11R)-1'-methyl-4'-phenylspiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidine]-3'-carboxylate + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With sodium methylate In dichloromethane at 20℃; for 4h;	A 96% B n/a

(S)-4-benzyl-3-(4-methoxyphenyl)oxazolidin-2-one → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With ammonium cerium (IV) nitrate In water; acetonitrile at 0℃; for 0.0833333h;	95%

(S)-4-benzyl-3-((1'S,2'S,3'R,7a'R)-1',7,8-trimethyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-ylcarbonyl)oxazolidin-2-one + carbonic acid dimethyl ester (616-38-6) → methyl (1'S,2'S,7a'R,11R)-1',7,8-trimethyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylate + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With sodium methylate In dichloromethane at 20℃; for 4h;	A 95% B n/a

(S)-4-benzyl-3-[(E)-2-(phenylsulfonyl)ethenyl]-1,3-oxazolidin-2-one → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With pyrrolidine In acetonitrile at 55℃; for 4.5h; Inert atmosphere;	94%

(S)-4-benzyl-3-((2'R,3'S,4'S)-1',4'-dimethylspiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidine]-3'-ylcarbonyl)oxazolidin-2-one + carbonic acid dimethyl ester (616-38-6) → methyl (3'S,4'S,11R)-1',4'-dimethylspiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidine]-3'-carboxylate + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With sodium methylate In dichloromethane at 20℃; for 4h;	A 92% B n/a

N-benzyloxyamine (622-33-3) + (S)-3-benzoyl-4-phenylmethyl-2-oxazolidinone (153729-83-0) → N-benzyloxy benzamide (3532-25-0) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With samarium(III) trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 0.5h;	A 91% B n/a

methanol (67-56-1) + (4S)-3-((3S,2R)-3-hydroxy-2-methyl-3-phenylpropanoyl)-4-benzyl-1,3-oxazolidin-2-one → (S)-4-Benzyl-2-oxazolidinone (90719-32-7) + (2R,3S)-methyl 3-hydroxy-2-methyl-3-phenylpropanoate (36041-80-2)

Conditions	Yield
With C17H23BN2O at 25℃; under 760.051 Torr; for 48h; Inert atmosphere; chemoselective reaction;	A 91% B 89%

(4S)-4-benzyl-1,3-oxazolidine-2-thione (131744-19-9, 145588-94-9) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With methyloxirane In chloroform at 150℃; for 1h; Inert atmosphere; Microwave irradiation;	90%
With sodium hydroxide; dihydrogen peroxide In water Ambient temperature;	56%

L-Phenylalaninol (3182-95-4) + urea (57-13-6) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
In N,N-dimethyl acetamide for 0.0333333h; Cyclization; microwave heating;	90%

carbon dioxide (124-38-9) + L-Phenylalaninol (3182-95-4) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With caesium carbonate In dimethylsulfoxide-d6 at 25 - 150℃; under 2280.15 Torr; for 24h; Schlenk technique; Autoclave;	90%
Stage #1: carbon dioxide; L-Phenylalaninol With N(Et)4(1+)*(2-pyrrolidone-anion) In acetonitrile at 20℃; for 1h; Carboxylation; Stage #2: With p-toluenesulfonyl chloride In acetonitrile at 20℃; Cyclization; Further stages.;	71%
With Hexamethylcyclotrisiloxane; tetrabutyl ammonium fluoride In dimethylsulfoxide-d6 at 150℃; under 760.051 Torr; for 9h; Reagent/catalyst; chemoselective reaction;	78 %Spectr.

L-Phenylalaninol (3182-95-4) + mononitrophenyl carbonate (81420-42-0) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With dmap In dichloromethane for 3h;	90%

(S,E)-4-benzyl-3-(3-oxobut-1-en-1-yl)oxazolidin-2-one (1441063-84-8) + 1-dodecylthiol (112-55-0) → C16H30OS + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 0.3h; Inert atmosphere;	A n/a B 90%

(3R)-3-[(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]hexanenitrile → (R)-3-(hydroxymethyl)hexanenitrile + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 2h;	A 89.2% B 1.05 g
With sodium tetrahydroborate; water In tetrahydrofuran at 20 - 40℃; for 2h;	A 89.2% B 1.05 g

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + propionyl chloride (79-03-8) → (S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5, 101711-78-8)

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With sodium hydride In tetrahydrofuran at 0℃; for 1.16667h; Stage #2: propionyl chloride In tetrahydrofuran at 0 - 20℃;	100%
With n-butyllithium In tetrahydrofuran	100%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;	99%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + propionic acid (802294-64-0) → (S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5, 101711-78-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	100%
With 2-chloro-1-methylpyridinium p-toluenesulfonate; triethylamine In dichloromethane at 20℃; for 7h;	94.4%
With triethylamine In tetrahydrofuran	80%
With 4-methyl-morpholine; chloroformic acid ethyl ester; lithium chloride In tetrahydrofuran
With 4-methyl-morpholine; chloroformic acid ethyl ester; lithium chloride In tetrahydrofuran

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + isopentanoyl chloride (108-12-3) → (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one (145589-03-3, 104266-90-2)

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium; triphenylmethane In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: isopentanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h; Stage #3: With potassium carbonate In tetrahydrofuran; hexane; water	100%
With triethylamine; dmap In dichloromethane at 0 - 10℃; for 0.5h;	95%
With dmap In dichloromethane; water at 0 - 10℃; for 0.5h;	95%

di-tert-butyl dicarbonate (24424-99-5) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (S)-3-(tert-butoxycarbonyl)-4-benzyl-2-oxazolidinone (132836-68-1)

Conditions	Yield
With dmap In acetonitrile at 25℃; for 0.116667h;	100%

pent-4-enoyl chloride (39716-58-0) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (4S)-4-benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one (104266-88-8)

Conditions	Yield
With n-butyllithium	100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: pent-4-enoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	99%
With n-butyllithium In tetrahydrofuran at -78 - 20℃;	97%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + 3-[dimethyl(phenyl)silyl]glutaric anhydride (196491-68-6) → 5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid

Conditions	Yield
In tetrahydrofuran at 30℃; for 24h;	100%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium In tetrahydrofuran; hexane 1.) -35 deg C, 10 min, 2.) -78 deg C, 1 h;	100%
With dmap In dichloromethane at 20℃;

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + 2-Bromoacetyl bromide (598-21-0) → 4S-3-(2-bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone (129549-13-9)

Conditions	Yield
With n-butyllithium at -78 - 20℃; for 0.5h;	100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 2-Bromoacetyl bromide In tetrahydrofuran; hexane at -78 - 20℃; for 16.5h; Inert atmosphere;	92%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78 - -60℃; for 0.5h; Stage #2: 2-Bromoacetyl bromide In tetrahydrofuran; hexane at -78℃; for 1h;	87%

6-bromohexanoic acid (4224-70-8) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (S)-4-benzyl-3-(6-bromo-1-oxohexyl)-2-oxazolidinone (203739-34-8)

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 6-bromohexanoic acid In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	100%
With n-butyllithium; pivaloyl chloride; triethylamine Multistep reaction;
Stage #1: 6-bromohexanoic acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -78 - 0℃; Stage #2: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (S)-3-amino-4-benzyl-1,3-oxazolan-2-one (299216-13-0)

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With potassium hydride Stage #2: With chloroamine In tert-butyl methyl ether	100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With sodium hydride In 1,4-dioxane; mineral oil at 60℃; for 1h; Stage #2: In 1,4-dioxane; mineral oil at 20℃; for 6h;	86%
With n-butyllithium; O-(diphenylphosphinyl)hydroxylamine In tetrahydrofuran; hexane at 20℃; for 6h;	80%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + Cinnamic acid (621-82-9) → (S)-4-benzyl-3-(6-(benzyloxy)hex-2-enoyl)oxazolidin-2-one (133812-18-7)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	100%

cyclopentanepropanoyl chloride (104-97-2) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (4S)-4-benzyl-3-(3-cyclopentylpropanoyl)-1,3-oxazolidin-2-one

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane	100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃;	100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;	90%

4-bromobutyroyl chloride (927-58-2) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (S)-4-benzyl-3-(4-bromobutanoyl)oxazolidin-2-one (1424402-18-5)

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromobutyroyl chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	100%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + valeric acid (109-52-4) → 3-(1-oxopentyl)-4(S)-(phenylmethyl)-2-oxazolidinone (143868-89-7)

Conditions	Yield
Stage #1: valeric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -10 - 15℃; for 2h; Large scale; Stage #2: (S)-4-Benzyl-2-oxazolidinone With lithium chloride at 20℃; Large scale;	100%
Stage #1: valeric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -20 - -15℃; for 1h; Inert atmosphere; Stage #2: (S)-4-Benzyl-2-oxazolidinone With lithium chloride In tetrahydrofuran at -20 - 20℃; for 16h; Solvent; Temperature; Reagent/catalyst;	98.12%
Stage #1: valeric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere; Stage #2: (S)-4-Benzyl-2-oxazolidinone With lithium chloride In tetrahydrofuran at 20 - 25℃; for 16h;	94%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + n-valeryl chloride (638-29-9) → 3-(1-oxopentyl)-4(S)-(phenylmethyl)-2-oxazolidinone (143868-89-7)

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -70 - -65℃; for 0.5h; Inert atmosphere; Stage #2: n-valeryl chloride In tetrahydrofuran at -75 - -65℃; for 1h;	99.9%
With dmap; triethylamine In dichloromethane at 0 - 10℃; for 3h; Large scale;	98%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: n-valeryl chloride In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;	95%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + acetyl chloride (75-36-5) → (S)-3-acetyl-4-benzyloxazolidin-2-one (132836-66-9)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0℃;	99%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;	94.5%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran Inert atmosphere; Stage #2: acetyl chloride at -78℃; for 0.5h; Inert atmosphere;	82%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + butyryl chloride (141-75-3) → (S)-4-benzyl-3-butyryloxazolidin-2-one (111292-87-6, 143097-11-4, 112459-79-7)

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: butyryl chloride In tetrahydrofuran at -78℃; for 3h;	99%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Stage #2: butyryl chloride In tetrahydrofuran at -78 - 20℃; for 2.25h;	98%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Stage #2: butyryl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 3.67h;	98%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + α-allyloxyacetyl pivaloyl anhydride (318488-46-9) → (4S)-3-(2-allyloxyethanoyl)-4-benzyloxazolidin-2-one (197721-28-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃;	99%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: α-allyloxyacetyl pivaloyl anhydride In tetrahydrofuran; hexane at -78 - 0℃; for 0.75h; Further stages.;	5.45 g
With n-butyllithium In tetrahydrofuran; diethyl ether at -78 - 0℃; for 0.75h;	10.0 g

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + C11H18O4 → (S)-3-<1-oxo-2-(but-3-enyl-1-oxy)>-4-benzyl-2-oxazolidinone (197721-29-2)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃;	99%
With n-butyllithium 1.) THF, -78 deg C, 10 min, 2.) THF, ether, a) -78 deg C, 15 min, b) from -78 deg C to 0 deg C, 30 min; Yield given; Multistep reaction;

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + C12H20O4 → (S)-3-<1-oxo-2-(pent-4-enyl-1-oxy)>-4-benzyl-2-oxazolidinone (197721-30-5)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃;	99%
With n-butyllithium 1.) THF, -78 deg C, 10 min, 2.) THF, ether, a) -78 deg C, 15 min, b) from -78 deg C to 0 deg C, 30 min; Yield given; Multistep reaction;

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + phenylacetaldehyde (122-78-1) → (4S)-4-benzyl-3-<(E)-2-phenylethenyl>-1,3-oxazolan-2-one

Conditions	Yield
With pyridinium p-toluenesulfonate In toluene Reflux; Dean-Stark;	99%
With 1,2,3-Benzotriazole; toluene-4-sulfonic acid In toluene for 48h; Heating;	62%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + phenylbutyric acid chloride (18496-54-3) → (S)-4-benzyl-3-(3-phenylbutanoyl)oxazolidin-2-one (170450-77-8)

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 0.5h; Inert atmosphere; Stage #2: phenylbutyric acid chloride In tetrahydrofuran; n-heptane at -78 - 0℃; for 3.5h;	99%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 0.5h; Inert atmosphere; Stage #2: phenylbutyric acid chloride In tetrahydrofuran; n-heptane at -78 - 0℃; for 3.5h;	99%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 0.5h; Inert atmosphere; Stage #2: phenylbutyric acid chloride In tetrahydrofuran at -78 - 0℃; for 3.5h;	99%
With n-butyllithium 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, from -78 deg C to RT; Yield given; Multistep reaction;
With n-butyllithium; triphenylmethane In tetrahydrofuran at -78℃;

4-Cyanochlorobenzene (623-03-0) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → 4-[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]benzonitrile

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; johnphos In toluene at 115℃; for 15h;	99%
With potassium phosphate; [(π-allyl)Pd(tBuBrettPhos)]OTf In tert-butyl alcohol at 110℃; for 3h; Schlenk technique; Inert atmosphere; Sealed tube;	95%
With (PAd2-DalPhos)NiCl(o-tol); caesium carbonate In 1,4-dioxane at 90℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;	64%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + n-valeryl chloride (638-29-9) → (R)-3-(1-valeroyl)-4-benzyloxazolidine-2-one

Conditions	Yield
With n-butyllithium In tetrahydrofuran; ethyl acetate	99%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + 3-cyclohexylpropionyl chloride (39098-75-4) → (4S)-3-(3-cyclohexyl-1-oxopropyl)-4-phenylmethyl-2-oxazolidinone (136187-43-4)

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 3-cyclohexylpropionyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	99%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 3-cyclohexylpropionyl chloride In tetrahydrofuran at -78 - 20℃;

Upstream product

• 14441-94-2 4-methoxy-1,3-oxazolidin-2-one 
• 6921-34-2 benzylmagnesium chloride 
• 13906-90-6 2-benzylaziridine 
• 124-38-9 carbon dioxide 
• 19881-97-1 3-phenylpropane-1,2-diol 
• 57-13-6 urea 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 1795-98-8 rac-phenylalaninol 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 79-22-1 methyl chloroformate 
• 108393-28-8 (2S,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-52-7 benzaldehyde 

Downstream Products

• 145589-03-3 (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 
• 128217-37-8 (4S)-3-<(2E)-hexenoyl>-4-phenylmethyl-1,3-oxazolidin-2-one 
• 152290-01-2 *,R^*)>-3,3'-(1,9-Dioxo-1,9-nonanediyl)bis<4-(phenylmethyl)-2-oxazolidinone> 
• 142635-38-9 (4S)-4-benzyl-3-(phenylthio)-2-isoxazolidinone 
• 104266-88-8 (4S)-4-benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one 
• 90719-30-5 (4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone 
• 112530-24-2 (4S)-3-((2'R)-2'-methylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone 
• 112530-23-1 (4S)-3-((2'S)-2'-methylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone 
• 104324-24-5 (4R)-3-((4'E)-4'-hexenoyl)-4-(phenylmethyl)-2-oxazolidinone 
• 156451-00-2 (S,E)-4-benzyl-3-(hex-4-enoyl)oxazolidin-2-one 
• 146232-49-7 (4R)-3-(5-bromovaleryl)-4-phenylmethyl-2-oxazolidinone 
• 156699-37-5 (S)-4-benzyl-3-(5-bromopentanoyl)oxazolidine-2-one 
• 119933-82-3 (4S)-3-(1,5-dioxo-5-methoxypentyl)-4-(phenylmethyl)-2-oxazolidinone 
• 142635-40-3 (4S)-4-benzyl-3-(tert-butylyhio)-2-isoxazolidinone 

Relevant articles and documents

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