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inquiryItems Standard Result Assay 98%min -----------------------------------------------------------------------------------------------
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inquiryUnique advantages Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White powder Storage:cool dry place Package:1kg/foil bag;25kg/drum Application:pharmaceutical intermediate Transpo
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inquiryProduct Description Product website: http://www.finerchem.com/pro01en/id/1625.html Product Name (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan
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inquiryName: (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan Synonyms: Empagliflozin intermediate CAS: 915095-94-2 MF: C17H16ClIO2 Appearance:White powder Storage:Store in cool and dry place, away from sun light. Package:25kg/drum Appli
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inquiry(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
With aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane In toluene at 0 - 23℃; for 2.5h; | 93% |
With aluminum (III) chloride; sodium tetrahydroborate In tetrahydrofuran for 5h; Reflux; | 90% |
With potassium borohydride; trifluoroacetic acid In tetrahydrofuran at 0 - 20℃; for 0.5h; | 85% |
4-(2-chloro-5-iodobenzyl)phenol
toluene-4-sulfonic acid (S)-(tetrahydrofuran-3-yl)ester
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; potassium iodide In acetonitrile at 50 - 55℃; Large scale; | 90.1% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Stage #1: (S)-3-(4-(5-iodo-2-aminobenzyl)phenoxy)tetrahydrofuran With hydrogenchloride; sodium nitrite In water at -10 - 0℃; for 2.5h; Stage #2: With hydrogenchloride; copper(l) chloride In water at 20 - 80℃; for 3h; | 75.2% |
fluorobenzene
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 2: potassium tert-butylate / tetrahydrofuran / 3 h / 16 - 25 °C 3: 1,1,3,3-Tetramethyldisiloxane / aluminum (III) chloride / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 1.2: 6 h / 20 - 30 °C 2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C 2.2: 1.83 h / 20 - 21 °C 3.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; aluminum (III) chloride / N,N-dimethyl-formamide / 25 - 45 °C / Industry scale 2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C / Industry scale 3.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C / Industry scale 3.2: 20 - 51 °C / Industry scale View Scheme | |
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h 1.2: 1 h / 0 - 5 °C 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 16 - 25 °C 3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 5 - 10 °C View Scheme |
2-chloro-5-iodobenzoic acid
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 2: potassium tert-butylate / tetrahydrofuran / 3 h / 16 - 25 °C 3: 1,1,3,3-Tetramethyldisiloxane / aluminum (III) chloride / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 1.2: 6 h / 20 - 30 °C 2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C 2.2: 1.83 h / 20 - 21 °C 3.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; aluminum (III) chloride / N,N-dimethyl-formamide / 25 - 45 °C / Industry scale 2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C / Industry scale 3.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C / Industry scale 3.2: 20 - 51 °C / Industry scale View Scheme |
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 3 h / 16 - 25 °C 2: 1,1,3,3-Tetramethyldisiloxane / aluminum (III) chloride / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C 1.2: 1.83 h / 20 - 21 °C 2.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C / Industry scale 2.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C / Industry scale 2.2: 20 - 51 °C / Industry scale View Scheme | |
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C 2: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 20 °C 2: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / 5 h / Reflux View Scheme |
2-chloro-5-iodobenzoylchloride
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aluminum (III) chloride / 1 h / 0 - 25 °C 2: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C 3: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C View Scheme | |
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 6 h / -5 °C 2: potassium tert-butylate / tetrahydrofuran / 20 °C 3: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / 5 h / Reflux View Scheme |
phenol
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: polyposphoric acid / 50 - 85 °C 2: potassium iodide; potassium carbonate / acetonitrile / 50 - 55 °C 3: potassium borohydride; trifluoroacetic acid / tetrahydrofuran / 0.5 h / 0 - 20 °C View Scheme |
(2-chloro-5-iodophenyl)(4-hydroxyphenyl)methanone
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium iodide; potassium carbonate / acetonitrile / 50 - 55 °C 2: potassium borohydride; trifluoroacetic acid / tetrahydrofuran / 0.5 h / 0 - 20 °C View Scheme |
4-hydroxybenzyl chloride
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sulfonyl chloride / dichloromethane / 3 h / -5 - 0 °C 1.2: 4.5 h / Reflux 2.1: zinc(II) chloride / ethyl acetate / 6 h / Reflux 3.1: hydrogenchloride; sodium nitrite / water / 2.5 h / -10 - 0 °C 3.2: 3 h / 20 - 80 °C View Scheme |
2-chloro-5-iodobenzoic acid
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: oxalyl chloride / dichloromethane; N,N-dimethyl-formamide / 4 h / 20 °C 1.2: 3 h / 0 - 20 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0 - 20 °C View Scheme |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; sodium nitrite / water / 2.5 h / -10 - 0 °C / Large scale 1.2: 1.5 h / 70 - 80 °C / Large scale 2.1: boron tribromide / dichloromethane / 1.5 h / -15 °C / Inert atmosphere; Large scale 3.1: N-ethyl-N,N-diisopropylamine; potassium iodide / acetonitrile / 50 - 55 °C / Large scale View Scheme |
p-methoxybenzyl chloride
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: zinc(II) chloride / ethyl acetate / 7 h / Reflux; Large scale 2.1: hydrogenchloride; sodium nitrite / water / 2.5 h / -10 - 0 °C / Large scale 2.2: 1.5 h / 70 - 80 °C / Large scale 3.1: boron tribromide / dichloromethane / 1.5 h / -15 °C / Inert atmosphere; Large scale 4.1: N-ethyl-N,N-diisopropylamine; potassium iodide / acetonitrile / 50 - 55 °C / Large scale View Scheme |
p-aminoiodobenzene
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: zinc(II) chloride / ethyl acetate / 7 h / Reflux; Large scale 2.1: hydrogenchloride; sodium nitrite / water / 2.5 h / -10 - 0 °C / Large scale 2.2: 1.5 h / 70 - 80 °C / Large scale 3.1: boron tribromide / dichloromethane / 1.5 h / -15 °C / Inert atmosphere; Large scale 4.1: N-ethyl-N,N-diisopropylamine; potassium iodide / acetonitrile / 50 - 55 °C / Large scale View Scheme |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-D-glucopyranoside
Conditions | Yield |
---|---|
Stage #1: (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at -25℃; for 1h; Inert atmosphere; | 96% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
C8CuF9
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 70℃; for 33h; | 96% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
pentafluoroethylcopper(I)
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; for 36h; Inert atmosphere; Sealed tube; Glovebox; | 93% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
1-chloro-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-2-(4-(R)-tetrahydrofuran-3-yloxy-benzyl)-benzene
Conditions | Yield |
---|---|
With bis(acetylacetonate)nickel(II); magnesium chloride; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; zinc In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere; Cooling with ice; | 90% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
(1,5-anhydro-2-deoxy-4,6-O-bis(tert-butylsilylidene)-3-O-triisopropylsilyl-D-arabino-hex-1-enitol)boronic acid pinacol ester
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water for 8h; Reflux; Inert atmosphere; Large scale; | 89% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
(2S,3R,4S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol
Conditions | Yield |
---|---|
Stage #1: (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With TurboGrignard In tetrahydrofuran at -30 - -20℃; for 1h; Inert atmosphere; Stage #2: With citric acid In tetrahydrofuran; water for 0.5h; Inert atmosphere; | 82.2% |
Stage #1: (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran With isopropylmagnesium chloride; lithium chloride In acetonitrile at -20 - -15℃; for 1h; Large scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In acetonitrile at -10 - 0℃; for 8h; Solvent; Large scale; |
Conditions | Yield |
---|---|
Stage #1: (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran With n-butyllithium In tetrahydrofuran; hexane at -60 - -50℃; for 0.833333h; Inert atmosphere; Stage #2: C18H42O6Si4 In tetrahydrofuran; hexane at -50℃; Inert atmosphere; Stage #3: With hydrogenchloride In isopropyl alcohol at 0 - 20℃; | 80% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
trans-4-Octene
Conditions | Yield |
---|---|
With nickel(II) bromide dimethoxyethane; potassium fluoride; Triethoxysilane; 2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole In N,N-dimethyl-formamide for 24h; Inert atmosphere; Sealed tube; regioselective reaction; | 78% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere; | 77.6% |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere; | 76.9% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
empagliflozin
Conditions | Yield |
---|---|
Stage #1: (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -21 - -15℃; for 1.83333h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In dichloromethane; acetonitrile at -25 - -13℃; for 2.91667h; | 73% |
Stage #1: (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -21 - -15℃; for 1.83333h; Industry scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at -25 - -18℃; for 2.91667h; Industry scale; Stage #3: With citric acid In water at -13 - 19℃; Product distribution / selectivity; Industry scale; | 73% |
Conditions | Yield |
---|---|
Stage #1: (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran With TurboGrignard In tetrahydrofuran at -10 - 0℃; Cooling with ice; Inert atmosphere; Stage #2: C41H34O12S With 2,6-bis((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)pyridine In tetrahydrofuran at 40 - 50℃; Inert atmosphere; | 73% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
With potassium fluoride; 6,6'-dimethyl-2,2'-bipyridine; nickel(II) bromide 2-methoxyethyl ether complex; Triethoxysilane; potassium iodide In N,N-dimethyl acetamide; acetonitrile at 30℃; for 18h; Sealed tube; regioselective reaction; | 67% |
methanesulfonic acid
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Stage #1: (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran With n-butyllithium In tetrahydrofuran; hexane; toluene at -72 - -60℃; for 0.5h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -72℃; for 2h; Inert atmosphere; Stage #3: methanesulfonic acid In tetrahydrofuran; methanol; hexane; toluene at 20℃; | 60.1% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
trifluorormethanesulfonic acid
1,3,5-trimethyl-benzene
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 30% |
Conditions | Yield |
---|---|
Stage #1: (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -23 - -22℃; for 0.333333h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at -20℃; for 2h; Stage #3: With ammonium chloride In tetrahydrofuran; water Product distribution / selectivity; |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
With TurboGrignard In tetrahydrofuran at -15 - 21℃; for 1.83333h; Product distribution / selectivity; |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C 2: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2 3: hydrogenchloride / isopropyl alcohol; methanol View Scheme | |
Multi-step reaction with 2 steps 1: lithium chloride; isopropylmagnesium chloride / tetrahydrofuran / -30 - -20 °C / Inert atmosphere; Large scale 2: hydrogenchloride / methanol; water / 4 h / 20 °C / Large scale View Scheme | |
Multi-step reaction with 2 steps 1.1: TurboGrignard / tetrahydrofuran / 1 h / -30 - -20 °C / Inert atmosphere 1.2: 0.5 h / Inert atmosphere 2.1: hydrogenchloride / water / 1 h / 20 - 30 °C View Scheme |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
empagliflozin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C 2: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2 3: hydrogenchloride / isopropyl alcohol; methanol 4: aluminum (III) chloride; triethylsilane / dichloromethane; acetonitrile / 0.5 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 3 steps 1: lithium chloride; isopropylmagnesium chloride / tetrahydrofuran / -30 - -20 °C / Inert atmosphere; Large scale 2: hydrogenchloride / methanol; water / 4 h / 20 °C / Large scale 3: aluminum (III) chloride; triethylsilane / acetonitrile; dichloromethane View Scheme | |
Multi-step reaction with 3 steps 1.1: TurboGrignard / tetrahydrofuran / 1 h / -30 - -20 °C / Inert atmosphere 1.2: 0.5 h / Inert atmosphere 2.1: hydrogenchloride / water / 1 h / 20 - 30 °C 3.1: aluminum (III) chloride; triethylsilane / dichloromethane; acetonitrile View Scheme |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C 2: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2 3: hydrogenchloride / isopropyl alcohol; methanol 4: triethylamine; dmap / tetrahydrofuran View Scheme |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C 2: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2 3: hydrogenchloride / isopropyl alcohol; methanol 4: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide View Scheme |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C 2: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2 3: hydrogenchloride / isopropyl alcohol; methanol 4: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide View Scheme |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C 2.1: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2 3.1: hydrogenchloride / isopropyl alcohol; methanol 4.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide 5.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0.5 h / 15 - 20 °C 5.2: 90 °C View Scheme | |
Multi-step reaction with 5 steps 1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C 2: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2 3: hydrogenchloride / isopropyl alcohol; methanol 4: triethylamine; dmap / tetrahydrofuran 5: aluminum (III) chloride; triethylsilane / dichloromethane; acetonitrile / 0.5 h / 15 - 20 °C View Scheme |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C 2: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2 3: hydrogenchloride / isopropyl alcohol; methanol 4: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide 5: aluminum (III) chloride; triethylsilane / dichloromethane; acetonitrile / 0.5 h / 15 - 20 °C View Scheme |
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