(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one supplier

: 189028-93-1
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With TarB-N02 In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With lithium borohydride In tetrahydrofuran for 0.666667h; Reagent/catalyst; enantioselective reaction;	96%
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at -5 - 0℃; for 4 - 6h; Stage #2: With sulfuric acid; dihydrogen peroxide In methanol; dichloromethane; water; toluene for 0.25h;	95%
Stage #1: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at -5 - 0℃; for 0.25h; Stage #2: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione In dichloromethane; toluene at -5 - 0℃; for 4 - 6h;	95%

: 108-05-4
vinyl acetate

: 1246853-48-4
(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

A: 1246853-49-5
(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Lipozyme TL IM In toluene at 20 - 40℃; Product distribution / selectivity;	A 68% B 74%
With Candida rugosa lipase In di-isopropyl ether at 35℃; for 120h; Solvent; Reagent/catalyst; Concentration; Enzymatic reaction;	A n/a B n/a

...Expand

: 189028-93-1
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

A: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

B: (4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

C: (S)-3-[(S)-5-(4-Fluoro-phenyl)-1,5-dihydroxy-pentyl]-4-phenyl-oxazolidin-2-one

Conditions

Conditions	Yield
With borane-THF; boron trifluoride diethyl etherate; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 25℃; Product distribution; Further Variations:; Catalysts; Temperatures; acid additives, water content;
With BH3-DEA; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 40℃;

...Expand

: 189028-93-1
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

A: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

B: (S)-3-[(S)-5-(4-Fluoro-phenyl)-1,5-dihydroxy-pentyl]-4-phenyl-oxazolidin-2-one

Conditions

Conditions	Yield
With sodium tetrahydroborate; dimethyl sulfate; N,N-diethylaniline; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 20℃; Product distribution; Further Variations:; Reagents; Temperatures;	A 13 g B n/a

: 189028-93-1
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

A: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

B: (4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 18 - 20℃; for 1h; Stage #2: With water; potassium carbonate In tetrahydrofuran; toluene at 20 - 30℃; for 0.5h;
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With sodium tetrahydroborate; chloro-trimethyl-silane; (R)-α,α-diphenylprolinol In tetrahydrofuran at 24℃; for 3h; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 4℃; for 0.5h; Product distribution / selectivity;	A n/a B n/a
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With sodium tetrahydroborate; chloro-trimethyl-silane; (R)-2-[bis(4-trifluorophenyl)hydroxymethyl]pyrrolidine In tetrahydrofuran at 24℃; for 3h; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 4℃; for 0.5h; Product distribution / selectivity;	A n/a B n/a
With chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II); formic acid/triethylamine complex 5:2 In tert-butyl methyl ether at 42℃; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; stereoselective reaction;	A n/a B n/a

: 67-63-0
isopropyl alcohol

: 189028-93-1
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
With magnesium sulfate In triethanolamine(chloride)

: C24H26FNO5

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction View Scheme

: C24H26FNO5

A: 1246853-49-5
(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: Candida rugosa lipase / di-isopropyl ether / 120 h / 35 °C / Enzymatic reaction View Scheme
Multi-step reaction with 3 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: triethylamine; dmap / dichloromethane / 4 h / 0 °C 3: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / pH 6.2 / Enzymatic reaction View Scheme

: C24H26FNO5

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction View Scheme

: C24H26FNO5

A: 1246853-49-5
(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: Candida rugosa lipase / di-isopropyl ether / 120 h / 35 °C / Enzymatic reaction View Scheme
Multi-step reaction with 3 steps 1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction 2: triethylamine; dmap / dichloromethane / 4 h / 0 °C 3: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / pH 6.2 / Enzymatic reaction View Scheme

: 1246853-48-4
(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

A: 1246853-49-5
(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 4 h / 0 °C 2: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / pH 6.2 / Enzymatic reaction View Scheme

: 140-11-4
Benzyl acetate

: 1246853-48-4
(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

A: 1246853-49-5
(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C: (4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions

Conditions	Yield
With Candida antarctica B lipase In toluene at 35℃; for 120h; Solvent; Reagent/catalyst; Enzymatic reaction;	A n/a B n/a C n/a

...Expand

: 108-05-4
vinyl acetate

: 1246853-48-4
(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

A: 1246853-49-5
(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C: (4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions

Conditions	Yield
With Candida antarctica B lipase In toluene at 35℃; for 120h; Solvent; Reagent/catalyst; Enzymatic reaction;	A n/a B n/a C n/a

...Expand

: (RS)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

A: 1246853-49-5
(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
With Candida rugosa lipase In aq. phosphate buffer; di-isopropyl ether at 40℃; for 120h; pH=6.2; Solvent; Reagent/catalyst; Temperature; pH-value; Concentration; Enzymatic reaction; enantioselective reaction;	A n/a B n/a

: 189028-93-1
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

A: 1246853-49-5
(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: borane-THF / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere 2: Candida rugosa lipase / di-isopropyl ether / 120 h / 35 °C / Enzymatic reaction View Scheme
Multi-step reaction with 3 steps 1: borane-THF / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere 2: triethylamine; dmap / dichloromethane / 4 h / 0 °C 3: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / pH 6.2 / Enzymatic reaction View Scheme

: 793673-93-5
(-)-6-(4-fluorophenyl)tetrahydro-2H-pyran-2-one

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C 2: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C 3: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C View Scheme

: (5S)-5-(4-fluorophenyl)-5-hydroxy-N-((S)-2-hydroxy-1-phenylethyl)pentanamide

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C 2: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C View Scheme

: tert-butyl (S)-5-(4-fluorophenyl)-5-hydroxypentanoyl((S)-2-hydroxy-1-phenylethyl)carbamate

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 4 - 20℃; for 2h;	800 mg

: 149437-76-3
5-(4-fluorophenyl)-5-oxopentanoic acid

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: sulfuric acid / 1 h / Reflux 2.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C 2.2: 2 h / 4 - 20 °C 3.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 4.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C 5.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C 6.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: triethylamine; pivaloyl chloride / dichloromethane / 2.5 h / 5 - 10 °C 1.2: 3 h / 15 - 45 °C 2.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 2.33 h / -10 - -5 °C 2.2: -10 - 0 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: sulfuric acid / 1 h / Reflux
2.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C
2.2: 2 h / 4 - 20 °C
3.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
4.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C
5.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C
View Scheme

Multi-step reaction with 2 steps
1.1: triethylamine; pivaloyl chloride / dichloromethane / 2.5 h / 5 - 10 °C
1.2: 3 h / 15 - 45 °C
2.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 2.33 h / -10 - -5 °C
2.2: -10 - 0 °C
View Scheme

: 462-06-6
fluorobenzene

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C 2.1: sulfuric acid / 1 h / Reflux 3.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C 3.2: 2 h / 4 - 20 °C 4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 5.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C 6.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C 7.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C
2.1: sulfuric acid / 1 h / Reflux
3.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C
3.2: 2 h / 4 - 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
5.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C
6.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C
7.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C
View Scheme

: (S)-5-(4-fluorophenyl)-5-hydroxypentanoic acid

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 2: dmap / 1,4-dioxane / 16 h / 55 - 60 °C 3: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C 4: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C View Scheme

: 108-55-4
glutaric anhydride,

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C 2.1: sulfuric acid / 1 h / Reflux 3.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C 3.2: 2 h / 4 - 20 °C 4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 5.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C 6.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C 7.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C
2.1: sulfuric acid / 1 h / Reflux
3.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C
3.2: 2 h / 4 - 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
5.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C
6.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C
7.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C
View Scheme

: 149437-67-2
5-(4-fluorophenyl)-5-oxopentanoic acid methyl ester

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C 1.2: 2 h / 4 - 20 °C 2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 3.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C 4.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C
1.2: 2 h / 4 - 20 °C
2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
3.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C
4.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C
View Scheme

: 99395-88-7
(S)-4-phenyl-2-oxazolidinone

: 149437-76-3
5-(4-fluorophenyl)-5-oxopentanoic acid

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Stage #1: 5-(4-fluorophenyl)-5-oxopentanoic acid With pivaloyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 4h; Stage #2: (S)-4-phenyl-2-oxazolidinone In N,N-dimethyl-formamide at 20℃; for 2h; Reflux; Stage #3: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane at 0 - 20℃; for 3h;

: 99395-88-7
(S)-4-phenyl-2-oxazolidinone

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine; pivaloyl chloride / dichloromethane / 2.5 h / 5 - 10 °C 1.2: 3 h / 15 - 45 °C 2.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 2.33 h / -10 - -5 °C 2.2: -10 - 0 °C View Scheme

: 75-77-4
chloro-trimethyl-silane

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: (S)-3-((S)-5-(4-fluorophenyl)-5-((trimethylsilyl)oxy)-pentanoyl)-4-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With triethylamine In tert-butyl methyl ether; toluene at -10 - 20℃; Inert atmosphere;	95%
Stage #1: chloro-trimethyl-silane; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10℃; for 1.5h; Stage #2: With titanium tetrachloride
With N-ethyl-N,N-diisopropylamine In dichloromethane at -10℃;

: 70627-52-0
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 1185883-39-9
C40H36F2N2O5

Conditions

Conditions	Yield
Stage #1: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -5℃; for 2h; Inert atmosphere; Stage #2: With titanium tetrachloride In dichloromethane at -30℃; for 2h; Inert atmosphere;	94%

: 75-77-4
chloro-trimethyl-silane

: 70627-52-0
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: C43H44F2N2O5Si

Conditions

Conditions	Yield
Stage #1: chloro-trimethyl-silane; 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 5℃; Inert atmosphere; Stage #2: With titanium tetrachloride In dichloromethane at -5 - 5℃; for 1h;	93%

...Expand

: 75-77-4
chloro-trimethyl-silane

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 272778-12-8
(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: chloro-trimethyl-silane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - 0℃; Inert atmosphere; Stage #2: With titanium tetrachloride In dichloromethane at -30 - -25℃; Inert atmosphere;	66.6%
With triethylamine In dichloromethane at -20℃; Reagent/catalyst; Solvent;

...Expand

: 75-77-4
chloro-trimethyl-silane

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 272778-12-8
(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: (E)-(4-hydroxy-benzylidene)-(4-fluorophenyl)-amine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃; Stage #2: chloro-trimethyl-silane In dichloromethane at -5℃; for 1.5h; Stage #3: With titanium tetrachloride In dichloromethane at -30 - -25℃; for 3h;	65%

: 75-77-4
chloro-trimethyl-silane

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: C39H46F2N2O5Si2

Conditions

Conditions	Yield
Stage #1: N-(4-hydroxybenzylidene)-4-fluorobenzenamine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃; Stage #2: chloro-trimethyl-silane In dichloromethane at -5℃; for 1.5h; Stage #3: With N,O-bis-(trimethylsilyl)-acetamide; titanium tetrachloride more than 3 stages;	65%

...Expand

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 107-30-2
chloromethyl methyl ether

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: C37H38F2N2O7

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -20 - -10℃; for 1h; Temperature; Reagent/catalyst;	64.5%

...Expand

: 18162-48-6
tert-butyldimethylsilyl chloride

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 937798-07-7
C26H34FNO4Si

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; Reagent/catalyst; Temperature;	62%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h;	42 g

: 70627-52-0
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: C40H36F2N2O5

Conditions

Conditions	Yield
With titanium(IV) isopropylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -30 - -20℃; for 5h;	60.9%

: 75-77-4
chloro-trimethyl-silane

: 10416-59-8
N,O-bis-(trimethylsilyl)-acetamide

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 272778-12-8
(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: chloro-trimethyl-silane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃; for 1h; Stage #2: With titanium tetrachloride In dichloromethane at -30℃; for 20h; Stage #3: N,O-bis-(trimethylsilyl)-acetamide	60%

...Expand

: 914777-35-8
N-{(1E)-[2-(benzyloxy)-4-bromophenyl]methylene}-N-phenylamine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 914777-36-9
(S)-3-[(2R,5S)-2-[(S)-(2-benzyloxy-4-bromo-phenyl)-phenylamino-methyl]-5-(4-fluoro-phenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane at -45 - -20℃; for 1h; Stage #2: With titanium tetrachloride In dichloromethane at -35 - -30℃; for 0.75h; Stage #3: N-{(1E)-[2-(benzyloxy)-4-bromophenyl]methylene}-N-phenylamine With acetic acid more than 3 stages;	51%
Stage #1: (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane at -45 - -20℃; for 1h; Stage #2: With titanium tetrachloride In dichloromethane at -45 - -30℃; for 1.08333h; Stage #3: N-{(1E)-[2-(benzyloxy)-4-bromophenyl]methylene}-N-phenylamine With acetic acid; tartaric acid more than 3 stages;	51%

Yield

Stage #1: (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane at -45 - -20℃; for 1h;
Stage #2: With titanium tetrachloride In dichloromethane at -35 - -30℃; for 0.75h;
Stage #3: N-{(1E)-[2-(benzyloxy)-4-bromophenyl]methylene}-N-phenylamine With acetic acid more than 3 stages;

51%

Stage #1: (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane at -45 - -20℃; for 1h;
Stage #2: With titanium tetrachloride In dichloromethane at -45 - -30℃; for 1.08333h;
Stage #3: N-{(1E)-[2-(benzyloxy)-4-bromophenyl]methylene}-N-phenylamine With acetic acid; tartaric acid more than 3 stages;

51%

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: C10(13)C6H18FNOSi

: C30(13)C6H38F2N2O5Si

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at -35 - -30℃; for 3h;

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-([12C6]-4-hydroxyphenyl)-2-azetidinone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: TiCl4 / CH2Cl2 / 3 h / -35 - -30 °C 2.1: 995 mg / CH2Cl2 / 0.5 h / Heating 3.1: BSA / CH2Cl2 / 0.25 h / 20 °C 3.2: TBAF*3H2O / CH2Cl2 / 90 h / 0 °C 3.3: 90 percent / aq. H2SO4 / propan-2-ol / 1 h View Scheme

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 438624-70-5
C33(13)C6H46F2N2O5Si2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: TiCl4 / CH2Cl2 / 3 h / -35 - -30 °C 2: 995 mg / CH2Cl2 / 0.5 h / Heating View Scheme

: 100-39-0
benzyl bromide

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 851860-27-0
(4S)-3-[(5S)-5-(benzyloxy)-5-(4-fluorophenyl)pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions

Conditions	Yield
With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.666667h;

: 75-77-4
chloro-trimethyl-silane

: 3230-41-9
4-{[(1E)-(4-iodophenyl)methylene]amino}phenol

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: C40H48FIN2O5Si2

Conditions

Conditions	Yield
Stage #1: 4-{[(1E)-(4-iodophenyl)methylene]amino}phenol; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 0℃; Stage #2: chloro-trimethyl-silane In dichloromethane at -25 - 0℃; for 1h; Stage #3: With titanium tetrachloride; sodium hydrogensulfite; rochelle salt more than 3 stages;

...Expand

: 75-77-4
chloro-trimethyl-silane

: 1078641-31-2
4-({(1E)-[2-(allyloxy)-4-bromophenyl]methylene}amino)phenol

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 1078641-32-3
(4S)-3-{(2R,5S)-2-{(S)-[2-(allyloxy)-4-bromophenyl][(4-hydroxyphenyl)amino]methyl}-5-(4-fluorophenyl)-5-[(trimethylsilyl)oxy]pentanoyl}-4-phenyl-1,3-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: chloro-trimethyl-silane; 4-({(1E)-[2-(allyloxy)-4-bromophenyl]methylene}amino)phenol; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -30 - 0℃; for 1h; Stage #2: With Rochelle's salt; sodium hydrogensulfite; acetic acid; titanium tetrachloride In dichloromethane; water at -30 - 20℃; Cooling with ice/salt; Stage #3: With N,O-bis-(trimethylsilyl)-acetamide at 45℃; for 0.5h;

Yield

Stage #1: chloro-trimethyl-silane; 4-({(1E)-[2-(allyloxy)-4-bromophenyl]methylene}amino)phenol; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -30 - 0℃; for 1h;
Stage #2: With Rochelle's salt; sodium hydrogensulfite; acetic acid; titanium tetrachloride In dichloromethane; water at -30 - 20℃; Cooling with ice/salt;
Stage #3: With N,O-bis-(trimethylsilyl)-acetamide at 45℃; for 0.5h;

...Expand

Reaxys ID: 19845323: Reaxys ID: 19845323

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Reaxys ID: 19845322: Reaxys ID: 19845322

Conditions

Conditions	Yield
With titanium tetrachloride; N-ethyl-N,N-diisopropylamine In dichloromethane

...Expand

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 163222-33-1
ezetemibe

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 °C 2.1: titanium tetrachloride / dichloromethane / 0.75 h / -40 °C 2.2: 19.5 h / -40 - -35 °C 3.1: acetic acid / dichloromethane / 1 h 3.2: 1 h / 0 °C 3.3: 1 h / 20 °C 4.1: toluene / 3 h / 90 °C 4.2: 14 h / 50 °C 5.1: hydrogenchloride; water; acetic acid; iron / ethanol / 0.5 h / 0 - 20 °C 6.1: sodium nitrite; sulfuric acid / N,N-dimethyl-formamide; water / 1.5 h / 0 °C 6.2: 0.42 h / 20 - 90 °C View Scheme
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; chloro-trimethyl-silane; titanium tetrachloride / dichloromethane / 2 h / -30 - -25 °C 1.2: 2 h / Reflux 2.1: bis-(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / tert-butyl methyl ether / 1.5 h / 20 °C 2.2: 0.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / -20 °C 2: H-ZSM-5 molecular sieve / -30 °C 3: perchloric acid / 3 h / 40 °C View Scheme

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: C36H37F2N3O6Si

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 °C 2.1: titanium tetrachloride / dichloromethane / 0.75 h / -40 °C 2.2: 19.5 h / -40 - -35 °C View Scheme

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 1354716-96-3
(4S)-phenyl-3-[(5S)-(4-fluorophenyl)-(2R)-[(1S)-(4-fluorophenylamino)-1-(4-nitrophenyl)methyl]-5-hydroxypentanoyl]oxazolidin-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 °C 2.1: titanium tetrachloride / dichloromethane / 0.75 h / -40 °C 2.2: 19.5 h / -40 - -35 °C 3.1: acetic acid / dichloromethane / 1 h 3.2: 1 h / 0 °C 3.3: 1 h / 20 °C View Scheme

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 1354716-97-4
1-(4-fluorophenyl)-(3R)-[(3S)-(4-fluorophenyl)-3-trimethylsilyloxypropyl]-(4S)-(4-nitrophenyl)azetidin-2-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 °C 2.1: titanium tetrachloride / dichloromethane / 0.75 h / -40 °C 2.2: 19.5 h / -40 - -35 °C 3.1: acetic acid / dichloromethane / 1 h 3.2: 1 h / 0 °C 3.3: 1 h / 20 °C 4.1: toluene / 3 h / 90 °C 4.2: 14 h / 50 °C View Scheme

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 1354716-98-5
(4S)-(4-aminophenyl)-1-(4-fluorophenyl)-(3R)-[(3S)-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 °C 2.1: titanium tetrachloride / dichloromethane / 0.75 h / -40 °C 2.2: 19.5 h / -40 - -35 °C 3.1: acetic acid / dichloromethane / 1 h 3.2: 1 h / 0 °C 3.3: 1 h / 20 °C 4.1: toluene / 3 h / 90 °C 4.2: 14 h / 50 °C 5.1: hydrogenchloride; water; acetic acid; iron / ethanol / 0.5 h / 0 - 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 °C
2.1: titanium tetrachloride / dichloromethane / 0.75 h / -40 °C
2.2: 19.5 h / -40 - -35 °C
3.1: acetic acid / dichloromethane / 1 h
3.2: 1 h / 0 °C
3.3: 1 h / 20 °C
4.1: toluene / 3 h / 90 °C
4.2: 14 h / 50 °C
5.1: hydrogenchloride; water; acetic acid; iron / ethanol / 0.5 h / 0 - 20 °C
View Scheme

Product Name

(4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE

Synthetic route

(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one Specification

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