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inquiry(3R,4S)-4-[4-(Benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one CAS No.:190595-65-4 Name: (3R,4S)-4-[4-(Benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azeti
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inquiry(3R,4S)-4-(4-benzyloxyphenyl)-1-(4-fluoro phenyl)-3-{2-[2-(4-fluorophenyl)-[1,3]-dioxolan-2-yl]ethyl}azetidin-2-one
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With water; toluene-4-sulfonic acid In acetone at 20℃; for 6h; Product distribution / selectivity; Reflux; | 99% |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
at 20℃; for 0.166667h; Temperature; | 91.6% |
(3R,4S)-4-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-3-{2-[2-(4-fluorophenyl)-5,5-dimethyl-[1,3]dioxan-2-yl]-ethyl}azetidin-2-one
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With formic acid In dichloromethane for 12h; Reflux; | 90% |
With sulfuric acid In water; isopropyl alcohol at 20 - 25℃; for 1h; Product distribution / selectivity; | 87.9% |
With acetic acid at 20 - 25℃; for 1h; Product distribution / selectivity; | 85.3% |
(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-((E)-3-(4-fluorophenyl)allyl)azetidin-2-one
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With perchloric acid; palladium diacetate; p-benzoquinone In water; acetonitrile for 16h; | 90% |
(S)-3-{4-[2-(4-fluorophenyl)dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride In toluene at 60℃; | 88.94% |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(Z)-3-(4-fluorophenyl)allyl]azetidin-2-one
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With perchloric acid; p-benzoquinone; palladium diacetate In water; acetonitrile for 48h; Inert atmosphere; | 86% |
With perchloric acid; water; palladium diacetate; p-benzoquinone In acetonitrile Wacker-Tsuji oxidation; Inert atmosphere; | 86% |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran at -20℃; for 0.666667h; | 77% |
With lithium hexamethyldisilazane In tetrahydrofuran at -20℃; for 0.666667h; | 77% |
3-[(2S,3R)-2-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-N-methoxy-N-methylpropaneamide
4-flourophenylmagnesium bromide
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene at 30 - 32℃; for 2.5h; Solvent; Temperature; | 75.7% |
(3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[(E)-3-(4-fluoro-phenyl)-3-oxo-propenyl]-azetidin-2-one
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With Wilkinson's catalyst; hydrogen In dichloromethane under 3102.89 Torr; for 18h; Hydrogenation; | 71% |
4-flourophenylmagnesium bromide
3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Stage #1: 4-flourophenylmagnesium bromide With zinc(II) chloride In tetrahydrofuran at 4℃; Stage #2: 3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 0℃; for 4.5h; | 37% |
With zinc(II) chloride; palladium diacetate In toluene at 0 - 20℃; for 2h; |
4-fluorophenylzinc bromide
3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 10℃; for 1h; Yield given; | |
palladium diacetate In toluene at 20℃; for 0.75h; | |
Stage #1: 4-fluorophenylzinc bromide; 3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride; palladium diacetate In toluene at 10 - 11℃; for 0.333333h; Stage #2: With hydrogenchloride; water In toluene |
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 64 percent / LDA; DMPU; LiCl / dimethylformamide; tetrahydrofuran / 18 h / -30 - -25 °C 2: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C 3: BF3 etherate / toluene / 0.08 h / -30 °C 4: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C 5: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr View Scheme | |
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -5 °C 2: N,O-Bis(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / toluene / 48 h / Reflux 3: formic acid / dichloromethane / 12 h / Reflux View Scheme |
(2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: BF3 etherate / toluene / 0.08 h / -30 °C 2: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C 3: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr View Scheme |
(3S,4S)-4-(4-Benzyloxy-phenyl)-3-((S)-1,2-dihydroxy-ethyl)-1-(4-fluoro-phenyl)-azetidin-2-one
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C 2: BF3 etherate / toluene / 0.08 h / -30 °C 3: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C 4: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr View Scheme |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: BF3 etherate / toluene / 0.08 h / -30 °C 2: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C 3: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr View Scheme |
(3S,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-hydroxy-3-oxo-propyl]-azetidin-2-one
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C 2: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr View Scheme |
(Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: (nBu)3N / heptane; toluene / 80 - 90 °C 2: LiOH*H2O / methanol / 2 h 3: oxalyl chloride / CH2Cl2 / 16 h / 22 °C 4: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C View Scheme |
(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: oxalyl chloride / CH2Cl2 / 16 h / 22 °C 2: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C View Scheme |
methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: LiOH*H2O / methanol / 2 h 2: oxalyl chloride / CH2Cl2 / 16 h / 22 °C 3: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: diethyl aluminiumcholoride / toluene / -12 - 20 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 1 h / 40 - 50 °C / Inert atmosphere 2.2: 1 h / -5 - 0 °C View Scheme |
1-Bromo-4-fluorobenzene
3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With magnesium; Iron acetylacetonate In tetrahydrofuran at -85 - -78℃; for 1.08333h; Purification / work up; | |
With iodine; magnesium; Iron acetylacetonate In tetrahydrofuran at -90 - -78℃; for 0.0333333h; Purification / work up; |
4-fluorophenylzinc chloride
3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 0 - 22℃; for 1.5h; |
4-fluorophenylzinc chloride
(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Stage #1: (3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Negishi coupling reaction; Stage #2: 4-fluorophenylzinc chloride With palladium diacetate In tetrahydrofuran; toluene at 10 - 11℃; for 0.333333h; Negishi coupling reaction; | 127.5 g |
C31H23F2NO3
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With hydrogen; Wilkinson's catalyst In dichloromethane under 3375.34 Torr; for 18h; |
3-[(2S,3R)-2-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-N-methoxy-N-methylpropaneamide
1-Bromo-4-fluorobenzene
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Stage #1: 1-Bromo-4-fluorobenzene With magnesium In tetrahydrofuran at 40 - 45℃; for 1h; Heating / reflux; Stage #2: 3-[(2S,3R)-2-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-N-methoxy-N-methylpropaneamide In tetrahydrofuran at 0 - 10℃; for 0.75 - 0.833333h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 10 - 15℃; | |
Stage #1: 1-Bromo-4-fluorobenzene With magnesium In tetrahydrofuran at 40 - 50℃; for 1h; Inert atmosphere; Stage #2: 3-[(2S,3R)-2-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-N-methoxy-N-methylpropaneamide In tetrahydrofuran at -5 - 0℃; for 1h; | 34.5 g |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
With hydrogenchloride; water In 1,4-dioxane; acetone at 90 - 95℃; for 6h; |
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydroxylamine hydrochloride / pyridine / 0 - 20 °C 2.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 0 °C 2.2: -15 °C 3.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 60 °C 3.2: 8 h / 60 °C 3.3: 20 h / 20 °C 4.1: hydrogenchloride; formaldehyd / water; tetrahydrofuran / 6 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: hydroxylamine hydrochloride / pyridine / 0 - 20 °C 2.1: dmap; 1H-imidazole / dichloromethane / 0.17 h / 20 °C 2.2: 5 h 3.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 0 °C 3.2: 3 h / -15 °C 4.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 60 °C 4.2: 8 h / 60 °C 5.1: hydrogenchloride; formaldehyd / water; tetrahydrofuran / 4 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: phosphorus pentoxide; sulfuric acid / dichloromethane / 5 h / Reflux 2: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -5 °C 3: N,O-Bis(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / toluene / 48 h / Reflux 4: formic acid / dichloromethane / 12 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / hexane / 6 h / 25 °C 2: N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride / toluene / 60 °C View Scheme |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 0 °C 1.2: -15 °C 2.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 60 °C 2.2: 8 h / 60 °C 2.3: 20 h / 20 °C 3.1: hydrogenchloride; formaldehyd / water; tetrahydrofuran / 6 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: dmap; 1H-imidazole / dichloromethane / 0.17 h / 20 °C 1.2: 5 h 2.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 0 °C 2.2: 3 h / -15 °C 3.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 60 °C 3.2: 8 h / 60 °C 4.1: hydrogenchloride; formaldehyd / water; tetrahydrofuran / 4 h / 20 °C View Scheme |
(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-(hydroxyimino)propyl)azetidin-2-one
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Stage #1: (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-(hydroxyimino)propyl)azetidin-2-one With hydrogenchloride; formaldehyd In tetrahydrofuran; water at 20℃; for 6h; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water; ethyl acetate |
(3R,4S)-4-(4-(benzyloxy)phenyl)-3-(3-(tert-butyldimethylsilyloxyimino)-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)azetidin-2-one
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Stage #1: (3R,4S)-4-(4-(benzyloxy)phenyl)-3-(3-(tert-butyldimethylsilyloxyimino)-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)azetidin-2-one With hydrogenchloride; formaldehyd In tetrahydrofuran; water at 20℃; for 4h; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water; ethyl acetate Product distribution / selectivity; |
(S)-3-(5-(tert-butyldimethylsilyloximino)-5-(4-fluorophenyl)pentanoyl)-4-phenyloxazolidin-2-one
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 0 °C 1.2: 3 h / -15 °C 2.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 60 °C 2.2: 8 h / 60 °C 3.1: hydrogenchloride; formaldehyd / water; tetrahydrofuran / 4 h / 20 °C View Scheme |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
Conditions | Yield |
---|---|
With formic acid; [(S,S)-teth-TsDpen RuCl]; triethylamine In ethylbenzene at 35 - 40℃; for 24h; Inert atmosphere; | 99.8% |
With methanesulfonic acid; dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; methyl tertiarybutylether; toluene at -25 - -20℃; for 2.5 - 3.5h; Product distribution / selectivity; | 98.04% |
With methanesulfonic acid; dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at -25 - -20℃; for 2.5 - 3.5h; Product distribution / selectivity; | 98.6% |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Stage #1: (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one With di-methylsulfide borane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at -10 - 20℃; for 2.5h; Inert atmosphere; Stage #2: With methanol In tetrahydrofuran for 0.5h; Inert atmosphere; | 98.7% |
With dimethylsulfide borane complex In dichloromethane |
2,2-Dimethyl-1,3-propanediol
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
(3R,4S)-4-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-3-{2-[2-(4-fluorophenyl)-5,5-dimethyl-[1,3]dioxan-2-yl]-ethyl}azetidin-2-one
Conditions | Yield |
---|---|
With Pyridine hydrobromide In toluene at 20 - 115℃; for 8h; Product distribution / selectivity; | 77.1% |
With pyridinium p-toluenesulfonate In toluene at 20 - 115℃; for 8h; Product distribution / selectivity; | 72% |
With toluene-4-sulfonic acid In toluene at 20 - 115℃; for 8h; Product distribution / selectivity; | 70.4% |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
[14C]-Sch 57871
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol under 3102.9 Torr; for 12h; | |
With hydrogen; palladium on activated charcoal In methanol under 2942.29 - 3310.08 Torr; |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
A
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
B
(3R,4S,3'R)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)-3-[3'-(4-fluorophenyl)-3'-hydroxy-propyl]-azetidin-2-one
Conditions | Yield |
---|---|
With dimethylsulfide borane complex In tetrahydrofuran at 22℃; for 3h; | A 0.141 g B n/a |
With dimethylsulfide borane complex In tetrahydrofuran at 22℃; for 3h; | |
Stage #1: (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one With sodium tetrahydroborate; chloro-trimethyl-silane; (R)-α,α-diphenylprolinol In tetrahydrofuran at 19 - 22℃; for 2.78333h; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 2℃; for 0.5h; Product distribution / selectivity; | A n/a B n/a |
With 1,1,1,3',3',3'-hexafluoro-propanol; C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; Overall yield = 99 %; enantioselective reaction; | A n/a B n/a |
With C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; Optical yield = 85 percent ee; enantioselective reaction; |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
ezetemibe
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C 2: 79 percent / ammonium formate; HOAc / Pd-C / methanol / 3 h / 45 - 55 °C / pH 3 - 5 View Scheme | |
Multi-step reaction with 2 steps 1: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 2: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr View Scheme | |
Multi-step reaction with 2 steps 1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / dichloromethane; tetrahydrofuran / 5 h / 0 °C 2: palladium on activated charcoal; hydrogen / methanol / 6 h / 20 °C / 3800.26 Torr View Scheme | |
Multi-step reaction with 2 steps 1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; dichloromethane / 5 h / 0 °C 2: palladium on activated charcoal; hydrogen / methanol / 6 h / 20 °C / 3800.26 Torr View Scheme | |
Multi-step reaction with 2 steps 1: dimethylsulfide borane complex / tetrahydrofuran / 4 h / -10 °C / Inert atmosphere 2: palladium on activated charcoal; formic acid; ammonium formate / isopropyl alcohol / 3 h / 40 °C View Scheme |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 2: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr 3: p-TsOH*H2O / toluene / 6 h / 80 °C View Scheme |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
(3R,4S)-1-(4-fluorophenyl)-3-[(3R)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 2: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr View Scheme |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
4(S)-(4-acetyloxyphenyl)-3(R)-(3(S)-acetyloxy-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)-2-azetidinone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 2: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr 3: 0.260 g / pyridine / CH2Cl2 / 1 h / 22 °C View Scheme |
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C 2: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr 3: pyridine / CH2Cl2 / 1 h / 22 °C View Scheme |
methanol
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran |
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