N-[(2R,3S)-2-(2,5-Difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester CAS No.:951127-25-6 Name: N-[(2R,3S)-2-(2,5-Difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-di
Cas:951127-25-6
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inquiryTert-butyl [(2R,3S)-5-oxo-2-(2,5-difluorophenyl)tetradihydro-2H-pyran-3-yl]carbamateAppearance:white or light yellow crystalline powder Storage:Store in a cool,dry place and keep away from direct strong light Package:according to customers' requireme
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inquiryN-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In water; ethyl acetate at 20℃; | 95% |
tert-butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With Dess-Martin periodane In dichloromethane at 0 - 30℃; for 4h; | 94.7% |
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 4h; | 94.7% |
With Dess-Martin periodane In dichloromethane at 0 - 4℃; for 4h; | 94.7% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With zinc(II) chloride In ethanol at 0℃; Inert atmosphere; Large scale; | 93.5% |
[(2R,3S)-5-methylene-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-yl]carbamic acid tert-butyl ester
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With sodium periodate; ruthenium(III) chloride trihydrate In dichloromethane; water; acetonitrile at 25℃; for 3h; | 84% |
With sodium periodate; rhodium(III) chloride | |
With sodium periodate; osmium(VIII) oxide In 1,4-dioxane; water at 0℃; for 2h; |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile at 20℃; for 1h; | 79% |
With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile at 20℃; for 0.5h; | 79% |
With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile at 20℃; for 1h; | 79% |
[(2R,3S)-5-hydroxy-5-hydroxymethyl-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-yl]carbamic acid tert-butyl ester
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With pyridine; lead(IV) acetate In methanol for 0.333333h; | |
With pyridine; lead(IV) acetate In methanol at 0℃; for 0.333333h; | |
With pyridine; lead(IV) tetraacetate In methanol at 0℃; for 0.333333h; |
2,5-difluorobenzoyl chloride
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: N-ethyl-N,N-diisopropylamine 2: sodium hydride 3: Heating 4: sodium tetrahydroborate 5: Chiralpak 1A / ethanol; hexane / Resolution of racemate 6: zinc; hydrogenchloride / water 7: ChiralCel AD 8: rhodium(III) chloride; sodium periodate View Scheme | |
Multi-step reaction with 9 steps 1: N-ethyl-N,N-diisopropylamine 2: sodium hydride 3: Heating 4: sodium tetrahydroborate 5: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol 6: Chiralpak 1A / ethanol; hexane / Resolution of racemate 7: zinc; hydrogenchloride / water 8: ChiralCel AD 9: rhodium(III) chloride; sodium periodate View Scheme |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: sodium hydride 2: Heating 3: sodium tetrahydroborate 4: Chiralpak 1A / ethanol; hexane / Resolution of racemate 5: zinc; hydrogenchloride / water 6: ChiralCel AD 7: rhodium(III) chloride; sodium periodate View Scheme | |
Multi-step reaction with 8 steps 1: sodium hydride 2: Heating 3: sodium tetrahydroborate 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol 5: Chiralpak 1A / ethanol; hexane / Resolution of racemate 6: zinc; hydrogenchloride / water 7: ChiralCel AD 8: rhodium(III) chloride; sodium periodate View Scheme |
6-(2,5-difluorophenyl)-3-methylidene-5-nitro-3,4-dihydro-2H-pyran
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sodium tetrahydroborate 2: Chiralpak 1A / ethanol; hexane / Resolution of racemate 3: zinc; hydrogenchloride / water 4: ChiralCel AD 5: rhodium(III) chloride; sodium periodate View Scheme | |
Multi-step reaction with 6 steps 1: sodium tetrahydroborate 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol 3: Chiralpak 1A / ethanol; hexane / Resolution of racemate 4: zinc; hydrogenchloride / water 5: ChiralCel AD 6: rhodium(III) chloride; sodium periodate View Scheme | |
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 5 °C 2: hydrogenchloride; zinc / water; ethanol / 1 h / 0 °C 3: methanol / 15 h / 25 °C 4: sodium carbonate / water; acetonitrile / 2 h / 0 - 30 °C 5: sodium periodate; ruthenium(III) chloride trihydrate / water; acetonitrile; dichloromethane / 3 h / 25 °C View Scheme |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: Chiralpak 1A / ethanol; hexane / Resolution of racemate 2: zinc; hydrogenchloride / water 3: ChiralCel AD 4: rhodium(III) chloride; sodium periodate View Scheme | |
Multi-step reaction with 4 steps 1: zinc; acetic acid / ethanol / 1 h 2: dichloromethane / 20 h / 20 °C 3: Chiralpak IA / Resolution of racemate 4: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C View Scheme |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol 2: Chiralpak 1A / ethanol; hexane / Resolution of racemate 3: zinc; hydrogenchloride / water 4: ChiralCel AD 5: rhodium(III) chloride; sodium periodate View Scheme |
(2R,3S)-5-methylidenyl-3-nitro-2-(2,5-difluorophenyl)tetrahydro-2H-pyran
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: zinc; hydrogenchloride / water 2: ChiralCel AD 3: rhodium(III) chloride; sodium periodate View Scheme | |
Multi-step reaction with 4 steps 1.1: zinc; hydrogenchloride / ethanol; water / 3 h 2.1: dichloromethane / 20 °C 3.1: osmium(VIII) oxide / acetone; quinoline; tert-butyl alcohol / 0.17 h / 20 °C 3.2: 48 h / 20 °C 4.1: sodium periodate / tetrahydrofuran; water / 4 h View Scheme | |
Multi-step reaction with 4 steps 1.1: zinc; hydrogenchloride / ethanol / 3 h 2.1: dichloromethane / 20 °C 3.1: osmium(VIII) oxide / acetone; water; tert-butyl alcohol / 0.17 h / 20 °C 3.2: 48 h / 20 °C 4.1: sodium periodate / tetrahydrofuran; water / 4 h View Scheme | |
Multi-step reaction with 4 steps 1.1: zinc; hydrogenchloride / water; ethanol / 3 h 2.1: dichloromethane / 20 °C 3.1: osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 0.17 h / 20 °C 3.2: 48 h / 20 °C 4.1: sodium iodate / water; tetrahydrofuran / 4 h View Scheme | |
Multi-step reaction with 4 steps 1.1: zinc; hydrogenchloride / water; ethanol / 3 h 2.1: dichloromethane / 20 °C 3.1: osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 0.17 h / 20 °C 3.2: 48 h / 20 °C 4.1: sodium periodate / water; tetrahydrofuran / 4 h View Scheme |
(2R,3S)-2-(2,5-difluorophenyl)-5-methylenetetrahydro-2H-pyran-3-amine
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ChiralCel AD 2: rhodium(III) chloride; sodium periodate View Scheme | |
Multi-step reaction with 3 steps 1.1: dichloromethane / 20 °C 2.1: tert-butyl alcohol; osmium(VIII) oxide / acetone; water; tert-butyl alcohol / 0.17 h / 20 °C 2.2: 48 h / 20 °C 3.1: sodium periodate / tetrahydrofuran; water / 4 h View Scheme | |
Multi-step reaction with 3 steps 1.1: dichloromethane / 20 °C 2.1: osmium(VIII) oxide / acetone; quinoline; tert-butyl alcohol / 0.17 h / 20 °C 2.2: 48 h / 20 °C 3.1: sodium periodate / tetrahydrofuran; water / 4 h View Scheme |
di-tert-butyl dicarbonate
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ChiralCel AD 2: rhodium(III) chloride; sodium periodate View Scheme | |
Multi-step reaction with 3 steps 1: dichloromethane / 20 h / 20 °C 2: Chiralpak IA / Resolution of racemate 3: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: sodium hydroxide / tert-butyl methyl ether; water / 4 h / 20 °C / Inert atmosphere 2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 15 - 25 °C / Inert atmosphere 2.2: 20 - 25 °C / Inert atmosphere 3.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere 3.2: 2.5 h / -10 - 20 °C / Inert atmosphere 4.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere 5.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere 6.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere 6.2: 15 - 25 °C / Inert atmosphere 7.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere View Scheme |
1-(2,5-difluorophenyl)-2-nitroethanone
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: Heating 2: sodium tetrahydroborate 3: Chiralpak 1A / ethanol; hexane / Resolution of racemate 4: zinc; hydrogenchloride / water 5: ChiralCel AD 6: rhodium(III) chloride; sodium periodate View Scheme | |
Multi-step reaction with 7 steps 1: Heating 2: sodium tetrahydroborate 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol 4: Chiralpak 1A / ethanol; hexane / Resolution of racemate 5: zinc; hydrogenchloride / water 6: ChiralCel AD 7: rhodium(III) chloride; sodium periodate View Scheme | |
Multi-step reaction with 6 steps 1: caesium carbonate / N,N-dimethyl acetamide / 4 h / 25 - 30 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 5 °C 3: hydrogenchloride; zinc / water; ethanol / 1 h / 0 °C 4: methanol / 15 h / 25 °C 5: sodium carbonate / water; acetonitrile / 2 h / 0 - 30 °C 6: sodium periodate; ruthenium(III) chloride trihydrate / water; acetonitrile; dichloromethane / 3 h / 25 °C View Scheme |
tert-butyl ((2R,3S)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl)carbamate
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: dimethylsulfide borane complex / tert-butyl methyl ether / 2 h / 0 - 10 °C 1.2: 7 h / 0 - 20 °C 2.1: sodiumtetraborate tetrahydrate; acetic acid; RuC13•3H20 / acetonitrile; water / 7.5 h / 0 °C / Inert atmosphere 2.2: 5.5 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere 1.2: 15 - 25 °C / Inert atmosphere 2.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Large scale 1.2: 0 - 20 °C / Large scale 2.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 15 h / 0 - 20 °C / Inert atmosphere; Large scale View Scheme |
tert-butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate
isopropyl alcohol
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbamate With RuC13•3H20; sodiumtetraborate tetrahydrate; acetic acid In water; acetonitrile at 0℃; for 7.5h; Inert atmosphere; Stage #2: isopropyl alcohol In water; acetonitrile at 0℃; for 5.5h; |
(±)-tert-butyl (1-(methoxy(methyl)amino)-1-oxopent-4-yn-2-yl)carbamate
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: isopropylmagnesium chloride / dichloromethane; tetrahydrofuran / 3 h 1.2: 12 h / -20 - 20 °C 2.1: 1,4-diaza-bicyclo[2.2.2]octane; Noyori's catalyst; formic acid / tert-butyl methyl ether; tetrahydrofuran / 45 °C / Inert atmosphere 3.1: tert-butylammonium hexafluorophosphate(V); sodium hydrogencarbonate; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); triphenylphosphine / tert-butyl methyl ether; N,N-dimethyl-formamide / 75 - 85 °C / Inert atmosphere 4.1: dimethylsulfide borane complex / tert-butyl methyl ether / 2 h / 0 - 10 °C 4.2: 7 h / 0 - 20 °C 5.1: sodiumtetraborate tetrahydrate; acetic acid; RuC13•3H20 / acetonitrile; water / 7.5 h / 0 °C / Inert atmosphere 5.2: 5.5 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere 1.2: 2.5 h / -10 - 20 °C / Inert atmosphere 2.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere 3.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere 4.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere 4.2: 15 - 25 °C / Inert atmosphere 5.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere 1.2: 2.5 h / -10 - 20 °C / Inert atmosphere 2.1: 1,4-diaza-bicyclo[2.2.2]octane; ((R,R)-Ts-DENEB)RuCl; formic acid / tetrahydrofuran / 10 - 35 °C / Inert atmosphere 3.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere 4.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere 4.2: 15 - 25 °C / Inert atmosphere 5.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere View Scheme |
(±)-tert-butyl (1-(2,5-difluorophenyl)-1-oxopent-4-yn-2-yl)carbamate
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 1,4-diaza-bicyclo[2.2.2]octane; Noyori's catalyst; formic acid / tert-butyl methyl ether; tetrahydrofuran / 45 °C / Inert atmosphere 2.1: tert-butylammonium hexafluorophosphate(V); sodium hydrogencarbonate; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); triphenylphosphine / tert-butyl methyl ether; N,N-dimethyl-formamide / 75 - 85 °C / Inert atmosphere 3.1: dimethylsulfide borane complex / tert-butyl methyl ether / 2 h / 0 - 10 °C 3.2: 7 h / 0 - 20 °C 4.1: sodiumtetraborate tetrahydrate; acetic acid; RuC13•3H20 / acetonitrile; water / 7.5 h / 0 °C / Inert atmosphere 4.2: 5.5 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere 2.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere 3.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere 3.2: 15 - 25 °C / Inert atmosphere 4.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: 1,4-diaza-bicyclo[2.2.2]octane; ((R,R)-Ts-DENEB)RuCl; formic acid / tetrahydrofuran / 10 - 35 °C / Inert atmosphere 2.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere 3.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere 3.2: 15 - 25 °C / Inert atmosphere 4.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere View Scheme |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: tert-butylammonium hexafluorophosphate(V); sodium hydrogencarbonate; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); triphenylphosphine / tert-butyl methyl ether; N,N-dimethyl-formamide / 75 - 85 °C / Inert atmosphere 2.1: dimethylsulfide borane complex / tert-butyl methyl ether / 2 h / 0 - 10 °C 2.2: 7 h / 0 - 20 °C 3.1: sodiumtetraborate tetrahydrate; acetic acid; RuC13•3H20 / acetonitrile; water / 7.5 h / 0 °C / Inert atmosphere 3.2: 5.5 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: 1-hydroxy-pyrrolidine-2,5-dione; tert-butylammonium hexafluorophosphate(V); sodium hydrogencarbonate / N,N-dimethyl-formamide / Inert atmosphere; Large scale 1.2: 75 - 85 °C / Inert atmosphere; Large scale 2.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Large scale 2.2: 0 - 20 °C / Large scale 3.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 15 h / 0 - 20 °C / Inert atmosphere; Large scale View Scheme |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride; zinc / water; ethanol / 1 h / 0 °C 2: methanol / 15 h / 25 °C 3: sodium carbonate / water; acetonitrile / 2 h / 0 - 30 °C 4: sodium periodate; ruthenium(III) chloride trihydrate / water; acetonitrile; dichloromethane / 3 h / 25 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: ChiralCel OD / Resolution of racemate 2.1: zinc; hydrogenchloride / ethanol; water / 3 h 3.1: dichloromethane / 20 °C 4.1: osmium(VIII) oxide / acetone; quinoline; tert-butyl alcohol / 0.17 h / 20 °C 4.2: 48 h / 20 °C 5.1: sodium periodate / tetrahydrofuran; water / 4 h View Scheme |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: isopropyl alcohol / 90 °C 2: hydrogenchloride; zinc / water; ethanol / 1 h / 0 °C 3: methanol / 15 h / 25 °C 4: sodium carbonate / water; acetonitrile / 2 h / 0 - 30 °C 5: sodium periodate; ruthenium(III) chloride trihydrate / water; acetonitrile; dichloromethane / 3 h / 25 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.5 h / 20 °C 2.1: zinc; hydrogenchloride / water; ethanol / 3 h 3.1: dichloromethane / 20 °C 4.1: osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 0.17 h / 20 °C 4.2: 48 h / 20 °C 5.1: sodium iodate / water; tetrahydrofuran / 4 h View Scheme | |
Multi-step reaction with 5 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.5 h / 20 °C 2.1: zinc; hydrogenchloride / water; ethanol / 3 h 3.1: dichloromethane / 20 °C 4.1: osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 0.17 h / 20 °C 4.2: 48 h / 20 °C 5.1: sodium periodate / water; tetrahydrofuran / 4 h View Scheme |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methanol / 15 h / 25 °C 2: sodium carbonate / water; acetonitrile / 2 h / 0 - 30 °C 3: sodium periodate; ruthenium(III) chloride trihydrate / water; acetonitrile; dichloromethane / 3 h / 25 °C View Scheme |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium carbonate / water; acetonitrile / 2 h / 0 - 30 °C 2: sodium periodate; ruthenium(III) chloride trihydrate / water; acetonitrile; dichloromethane / 3 h / 25 °C View Scheme |
2,5-difluorobenzaldehyde
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: sodium hydroxide / methanol; water / 0.5 h / 0 °C 2: Jones reagent / acetone / 0 - 10 °C 3: caesium carbonate / N,N-dimethyl acetamide / 4 h / 25 - 30 °C 4: sodium tetrahydroborate / methanol / 1 h / 0 - 5 °C 5: hydrogenchloride; zinc / water; ethanol / 1 h / 0 °C 6: methanol / 15 h / 25 °C 7: sodium carbonate / water; acetonitrile / 2 h / 0 - 30 °C 8: sodium periodate; ruthenium(III) chloride trihydrate / water; acetonitrile; dichloromethane / 3 h / 25 °C View Scheme | |
Multi-step reaction with 8 steps 1: sodium hydroxide / methanol / 1 h / 5 °C 2: Dess-Martin periodane / dichloromethane / 2.5 h / 10 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C 4: silica gel; sodium tetrahydroborate / chloroform; isopropyl alcohol / 2 h / 20 °C 5: zinc; acetic acid / ethanol / 1 h 6: dichloromethane / 20 h / 20 °C 7: Chiralpak IA / Resolution of racemate 8: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: sodium hydroxide / methanol / 5 °C 2.1: Dess-Martin periodane / dichloromethane / 24.5 h / 10 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C 4.1: silica gel; sodium tetrahydroborate / chloroform; isopropyl alcohol / 20 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.5 h / 20 °C 6.1: ChiralCel OD / Resolution of racemate 7.1: zinc; hydrogenchloride / ethanol; water / 3 h 8.1: dichloromethane / 20 °C 9.1: tert-butyl alcohol; osmium(VIII) oxide / acetone; water; tert-butyl alcohol / 0.17 h / 20 °C 9.2: 48 h / 20 °C 10.1: sodium periodate / tetrahydrofuran; water / 4 h View Scheme |
1-(2,5-difluorophenyl)-2-nitroethanol
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: Jones reagent / acetone / 0 - 10 °C 2: caesium carbonate / N,N-dimethyl acetamide / 4 h / 25 - 30 °C 3: sodium tetrahydroborate / methanol / 1 h / 0 - 5 °C 4: hydrogenchloride; zinc / water; ethanol / 1 h / 0 °C 5: methanol / 15 h / 25 °C 6: sodium carbonate / water; acetonitrile / 2 h / 0 - 30 °C 7: sodium periodate; ruthenium(III) chloride trihydrate / water; acetonitrile; dichloromethane / 3 h / 25 °C View Scheme | |
Multi-step reaction with 7 steps 1: Dess-Martin periodane / dichloromethane / 2.5 h / 10 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C 3: silica gel; sodium tetrahydroborate / chloroform; isopropyl alcohol / 2 h / 20 °C 4: zinc; acetic acid / ethanol / 1 h 5: dichloromethane / 20 h / 20 °C 6: Chiralpak IA / Resolution of racemate 7: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: Dess-Martin periodane / dichloromethane / 24.5 h / 10 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C 3.1: silica gel; sodium tetrahydroborate / chloroform; isopropyl alcohol / 20 °C 4.1: ChiralCel OD / Resolution of racemate 5.1: zinc; hydrogenchloride / ethanol; water / 3 h 6.1: dichloromethane / 20 °C 7.1: tert-butyl alcohol; osmium(VIII) oxide / acetone; water; tert-butyl alcohol / 0.17 h / 20 °C 7.2: 48 h / 20 °C 8.1: sodium periodate / tetrahydrofuran; water / 4 h View Scheme |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dichloromethane / 20 h / 20 °C 2: Chiralpak IA / Resolution of racemate 3: sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 0 °C View Scheme |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: dimethylsulfide borane complex / tert-butyl methyl ether; toluene / 3 h / -7 - 15 °C 2.1: acetic acid; ruthenium trichloride; sodium bromate / water; acetonitrile / 0 °C 2.2: 5 h / 0 °C View Scheme |
D,L-propargylglycine
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: sodium hydroxide / tert-butyl methyl ether; water / 4 h / 20 °C / Inert atmosphere 2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 15 - 25 °C / Inert atmosphere 2.2: 20 - 25 °C / Inert atmosphere 3.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere 3.2: 2.5 h / -10 - 20 °C / Inert atmosphere 4.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) / tetrahydrofuran / Inert atmosphere 5.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere 6.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere 6.2: 15 - 25 °C / Inert atmosphere 7.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 7 steps 1.1: sodium hydroxide / tert-butyl methyl ether; water / 4 h / 20 °C / Inert atmosphere 2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 15 - 25 °C / Inert atmosphere 2.2: 20 - 25 °C / Inert atmosphere 3.1: TurboGrignard / tetrahydrofuran; toluene / 2.5 h / -10 - -5 °C / Inert atmosphere 3.2: 2.5 h / -10 - 20 °C / Inert atmosphere 4.1: 1,4-diaza-bicyclo[2.2.2]octane; ((R,R)-Ts-DENEB)RuCl; formic acid / tetrahydrofuran / 10 - 35 °C / Inert atmosphere 5.1: tert-butylammonium hexafluorophosphate(V); 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II) ethanol; triphenylphosphine / N,N-dimethyl-formamide; n-heptane / 16 h / 80 °C / Inert atmosphere 6.1: dimethylsulfide borane complex / tert-butyl methyl ether / 0 - 5 °C / Inert atmosphere 6.2: 15 - 25 °C / Inert atmosphere 7.1: acetic acid; ruthenium(III) chloride trihydrate; sodium bromate / water; acetonitrile / 0 - 2 °C / Inert atmosphere View Scheme |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; ethyl (S)-1-(methylsulfonyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-4-carboxylate With benzenesulfonic acid In N,N-dimethyl acetamide at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 20℃; for 16h; | 100% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 0 - 20℃; for 8h; Inert atmosphere; | 99% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
4-methoxy-aniline
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; 4-methoxy-aniline In trifluoroacetic acid at 0℃; for 1h; Stage #2: With N,N-dimethyl acetamide; sodium tris(acetoxy)borohydride at 0 - 2℃; for 5h; pH=9; | 98% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
t-butoxycarbonylhydrazine
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; t-butoxycarbonylhydrazine With sodium cyanoborohydride at 25℃; for 0.166667h; Stage #2: With sodium cyanoborohydride at 25℃; for 16h; | 94.9% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate
tert-butyl ((2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl)tetrahydro-2H-pyran-3-yl)carbamate
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at -10℃; for 2h; | 94% |
With sodium tris(acetoxy)borohydride; acetic acid In N,N-dimethyl acetamide at -15℃; Reagent/catalyst; | 93.2% |
With sodium tris(acetoxy)borohydride; orthoformic acid triethyl ester In N,N-dimethyl acetamide at 5 - 50℃; for 12h; Solvent; Temperature; Inert atmosphere; Large scale; | 82.5% |
With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 0 - 20℃; for 7.66667h; Large scale; | |
With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 0 - 20℃; for 7.66667h; Large scale; |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; 3-bromo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine hydrochloride With N,N`-dimethylethylenediamine In N,N-dimethyl acetamide at 20℃; for 0.25h; Stage #2: With acetic acid In N,N-dimethyl acetamide for 0.25h; Stage #3: With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at -10 - 20℃; | 93.82% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; C7H8O3S*C10H11N3O2S2 In N,N-dimethyl acetamide at 20℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride at 0 - 20℃; for 12h; Inert atmosphere; | 92% |
pyrrolidin-3-ol
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: pyrrolidin-3-ol; N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester In methanol at 20℃; for 1h; Stage #2: With nido-decaborane In methanol at 20℃; | 90% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; acetic acid; triethylamine In N,N-dimethyl acetamide at 20℃; for 2.5h; | 88% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; 1-ethyl-1,4,5,6-tetrahydropyrrolo[3,4-d]imidazole-2-carbonitrile benzenesulfonate In N,N-dimethyl acetamide at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 0 - 20℃; for 2h; | 87% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
ethane-1,2-dithiol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere; Sealed tube; | 86% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
ethane-1,2-dithiol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Inert atmosphere; Sealed tube; | 86% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; 1-(difluoromethyl)-2-(1-methyl-1H-tetrazol-5-yl)-1,4,5,6-tetrahydropyrrolo[3,4-d]imidazole benzenesulfonate In N,N-dimethyl acetamide at 20℃; for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 0 - 20℃; for 2.5h; | 85% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
5-bromo-2,3-dihydro-1H-isoindole hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; 5-bromo-2,3-dihydro-1H-isoindole hydrochloride With triethylamine In N,N-dimethyl acetamide at 10℃; for 0.25h; Stage #2: With acetic acid In N,N-dimethyl acetamide for 1h; Stage #3: With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 0 - 10℃; for 16h; | 84.4% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; 1-ethyl-N-methoxy-N-methyl-1,4,5,6-tetrahydropyrrolo[3,4-d]imidazole-2-carboxamide benzenesulfonate In N,N-dimethyl acetamide at 20℃; for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 20℃; for 2.5h; | 82% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; 7-methanesulfonyl-2,7-diazaspiro[3.4]octane hydrochloride In methanol at 0℃; for 6h; Inert atmosphere; Stage #2: With diborane In methanol at 20℃; for 12h; Inert atmosphere; | 81% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
tert-butyl ((2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl)tetrahydro-2H-pyran-3-yl)carbamate
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at -10℃; | 80% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; C10H13N5*2C7H8O3S In N,N-dimethyl acetamide at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 20℃; for 2h; | 80% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; 2-((methylsulfonyl)methyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole benzenesulfonate In N,N-dimethyl acetamide at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 20℃; for 16h; | 79.7% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; 1-ethyl-2-(methylsulfonyl)-1,4,5,6-tetrahydropyrrolo[3,4-d]imidazole benzenesulfonate In N,N-dimethyl acetamide at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 0 - 20℃; for 16h; | 79% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; C7H8O3S*C9H9N3O2S2 In N,N-dimethyl acetamide at 20℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride at 0 - 20℃; for 12h; Inert atmosphere; | 79% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; C7H12N4O2S With nido-decaborane In methanol at 20℃; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 2h; | 78% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
t-butoxycarbonylhydrazine
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; t-butoxycarbonylhydrazine With acetic acid at 25℃; for 0.166667h; Stage #2: With sodium cyanoborohydride at 25℃; for 3h; | 76.9% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 20℃; for 3h; | 72% |
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Stage #1: N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester; 2,3,4,5,6,7-hexahydropyrrolo[3',4':3,4]pyrazolo[1,5-b][1,2]thiazine-1,1-dioxide p-toluenesulfonate With triethylamine In N,N-dimethyl acetamide at 20℃; for 3h; Stage #2: With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 20℃; Cooling with ice; | 71% |
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