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inquiry(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
With C63H78IrNOP(2+)*C32H12BF24(1-); hydrogen; caesium carbonate In methanol at 60℃; under 4560.31 Torr; for 12h; Autoclave; enantioselective reaction; | 99% |
(S)-methyl 6-fluorochroman-2-carboxylate
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: (S)-methyl 6-fluorochroman-2-carboxylate With sodium hydroxide In tetrahydrofuran; methanol; water at 0 - 20℃; for 6h; Schlenk technique; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water Schlenk technique; | 95% |
5-fluoro-2-hydroxybenzaldehyde
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C / Schlenk technique 2.1: potassium tert-butylate / tetrahydrofuran / 0 °C / Schlenk technique 3.1: hydrogenchloride / tetrahydrofuran; water / Schlenk technique; Reflux 4.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Schlenk technique 5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / Schlenk technique 6.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 7.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 8.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 9.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C35H30N2O2 / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 10.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 10.2: Schlenk technique View Scheme | |
Multi-step reaction with 10 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C / Schlenk technique 2.1: potassium tert-butylate / tetrahydrofuran / 0 °C / Schlenk technique 3.1: hydrogenchloride / tetrahydrofuran; water / Schlenk technique; Reflux 4.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Schlenk technique 5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / Schlenk technique 6.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 7.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 8.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 9.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; C23H22N2O2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 10.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 10.2: Schlenk technique View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / Schlenk technique 2.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 3.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 4.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 5.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C35H30N2O2 / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 6.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 6.2: Schlenk technique View Scheme | |
Multi-step reaction with 6 steps 1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / Schlenk technique 2.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 3.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 4.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 5.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; C23H22N2O2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 6.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 6.2: Schlenk technique View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: hydrogenchloride / tetrahydrofuran; water / Schlenk technique; Reflux 2.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Schlenk technique 3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / Schlenk technique 4.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 6.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 7.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C35H30N2O2 / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 8.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 8.2: Schlenk technique View Scheme | |
Multi-step reaction with 8 steps 1.1: hydrogenchloride / tetrahydrofuran; water / Schlenk technique; Reflux 2.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Schlenk technique 3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / Schlenk technique 4.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 6.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 7.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; C23H22N2O2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 8.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 8.2: Schlenk technique View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 3.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 4.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C35H30N2O2 / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 5.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 5.2: Schlenk technique View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 3.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 4.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; C23H22N2O2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 5.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 5.2: Schlenk technique View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 2.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C35H30N2O2 / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 3.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 3.2: Schlenk technique View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 2.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; C23H22N2O2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 3.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 3.2: Schlenk technique View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C35H30N2O2 / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 2.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 2.2: Schlenk technique View Scheme | |
Multi-step reaction with 2 steps 1.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; C23H22N2O2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 2.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 2.2: Schlenk technique View Scheme |
2-(benzyloxy)-5-fluorobenzaldehyde
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0 °C / Schlenk technique 2.1: hydrogenchloride / tetrahydrofuran; water / Schlenk technique; Reflux 3.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Schlenk technique 4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / Schlenk technique 5.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 6.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 7.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 8.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C35H30N2O2 / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 9.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 9.2: Schlenk technique View Scheme | |
Multi-step reaction with 9 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0 °C / Schlenk technique 2.1: hydrogenchloride / tetrahydrofuran; water / Schlenk technique; Reflux 3.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Schlenk technique 4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / Schlenk technique 5.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 6.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 7.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 8.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; C23H22N2O2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 9.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 9.2: Schlenk technique View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Schlenk technique 2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / Schlenk technique 3.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 4.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 5.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 6.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C35H30N2O2 / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 7.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 7.2: Schlenk technique View Scheme | |
Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Schlenk technique 2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / Schlenk technique 3.1: sodium hydride / mineral oil; tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 4.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 5.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 6.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; C23H22N2O2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 7.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 7.2: Schlenk technique View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 2.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 3.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C35H30N2O2 / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 4.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 4.2: Schlenk technique View Scheme | |
Multi-step reaction with 4 steps 1.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / Schlenk technique 2.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / Schlenk technique 3.1: tetrakis(actonitrile)copper(I) hexafluorophosphate; C23H22N2O2; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 0.08 h / 25 °C / Inert atmosphere; Schlenk technique; Glovebox 4.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / Schlenk technique 4.2: Schlenk technique View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - -30 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 2.1: dihydrogen peroxide / tetrahydrofuran; hexane / 3 h / 0 °C / Inert atmosphere 3.1: sodium hydroxide / water; methanol / 5 h / 50 °C 4.1: caesium carbonate; hydrogen; C63H78IrNOP(2+)*C32H12BF24(1-) / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dihydrogen peroxide / tetrahydrofuran; hexane / 3 h / 0 °C / Inert atmosphere 2: sodium hydroxide / water; methanol / 5 h / 50 °C 3: caesium carbonate; hydrogen; C63H78IrNOP(2+)*C32H12BF24(1-) / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water; methanol / 5 h / 50 °C 2: caesium carbonate; hydrogen; C63H78IrNOP(2+)*C32H12BF24(1-) / methanol / 12 h / 60 °C / 4560.31 Torr / Autoclave View Scheme |
Conditions | Yield |
---|---|
With calcium oxide In dimethyl sulfoxide at 160℃; for 5h; | 90% |
Conditions | Yield |
---|---|
With potassium hydroxide In N,N-dimethyl-formamide; toluene at 150℃; for 5h; | 86% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In toluene at 100℃; for 5.5h; | 85% |
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 5h; | 82% |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
With triethylamine; HATU In N,N-dimethyl-formamide | 30% |
With triethylamine; HATU In N,N-dimethyl-formamide | 30% |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
With thionyl chloride In toluene at 65 - 70℃; | |
With thionyl chloride In toluene at 65 - 70℃; |
(S)-6-fluorochroman-2-carboxylic acid
2-chloro-1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pivaloyl chloride; dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 - 50 °C / Large scale 2: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale 3: sodium phosphate; sulfuryl dichloride / ethyl acetate / 10 °C / Large scale 4: acetic acid; hydrogenchloride / water / 7 h / 30 - 40 °C / Large scale View Scheme | |
Multi-step reaction with 5 steps 1: thionyl chloride / toluene / 65 - 70 °C 2: pyridine / dichloromethane / 6 h / 0 - 25 °C 3: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale 4: sodium phosphate; sulfuryl dichloride / ethyl acetate / 10 °C / Large scale 5: acetic acid; hydrogenchloride / water / 7 h / 30 - 40 °C / Large scale View Scheme | |
Multi-step reaction with 4 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.33 h / 20 - 25 °C / Large scale 1.2: 20 - 50 °C / Large scale 2.1: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale 3.1: sulfuryl dichloride; sodium phosphate / ethyl acetate / 10 - 20 °C 4.1: hydrogenchloride / water; ethyl acetate; acetic acid / 3 h / 40 °C View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
(R)-2-chloro-1-((S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: pivaloyl chloride; dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 - 50 °C / Large scale 2: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale 3: sodium phosphate; sulfuryl dichloride / ethyl acetate / 10 °C / Large scale 4: acetic acid; hydrogenchloride / water / 7 h / 30 - 40 °C / Large scale 5: isopropyl alcohol; NAD; (R)-selective alcohol dehydrogenase / aq. buffer / 24 h / 0 - 25 °C / pH 6.99 / Enzymatic reaction View Scheme | |
Multi-step reaction with 6 steps 1: thionyl chloride / toluene / 65 - 70 °C 2: pyridine / dichloromethane / 6 h / 0 - 25 °C 3: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale 4: sodium phosphate; sulfuryl dichloride / ethyl acetate / 10 °C / Large scale 5: acetic acid; hydrogenchloride / water / 7 h / 30 - 40 °C / Large scale 6: isopropyl alcohol; NAD; (R)-selective alcohol dehydrogenase / aq. buffer / 24 h / 0 - 25 °C / pH 6.99 / Enzymatic reaction View Scheme | |
Multi-step reaction with 5 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.33 h / 20 - 25 °C / Large scale 1.2: 20 - 50 °C / Large scale 2.1: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale 3.1: sulfuryl dichloride; sodium phosphate / ethyl acetate / 10 - 20 °C 4.1: hydrogenchloride / water; ethyl acetate; acetic acid / 3 h / 40 °C 5.1: hydrogenchloride; NAD; triethanolamine; zinc(II) chloride / isopropyl alcohol; water; glycerol / 24 h / 0 - 25 °C / pH 6.99 / Enzymatic reaction View Scheme | |
Multi-step reaction with 6 steps 1: thionyl chloride / toluene / 65 - 70 °C 2: pyridine / dichloromethane / 6 h / 0 - 25 °C 3: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale 4: sulfuryl dichloride; sodium phosphate / ethyl acetate / 10 - 20 °C 5: hydrogenchloride / water; ethyl acetate; acetic acid / 3 h / 40 °C 6: hydrogenchloride; NAD; triethanolamine; zinc(II) chloride / isopropyl alcohol; water; glycerol / 24 h / 0 - 25 °C / pH 6.99 / Enzymatic reaction View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / toluene / 65 - 70 °C 2: pyridine / dichloromethane / 6 h / 0 - 25 °C View Scheme | |
Multi-step reaction with 2 steps 1: thionyl chloride / toluene / 65 - 70 °C 2: pyridine / dichloromethane / 6 h / 0 - 25 °C View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pivaloyl chloride; dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 - 50 °C / Large scale 2: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale View Scheme | |
Multi-step reaction with 3 steps 1: thionyl chloride / toluene / 65 - 70 °C 2: pyridine / dichloromethane / 6 h / 0 - 25 °C 3: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale View Scheme | |
Multi-step reaction with 2 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.33 h / 20 - 25 °C / Large scale 1.2: 20 - 50 °C / Large scale 2.1: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale View Scheme | |
Multi-step reaction with 3 steps 1: thionyl chloride / toluene / 65 - 70 °C 2: pyridine / dichloromethane / 6 h / 0 - 25 °C 3: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale View Scheme |
(S)-6-fluorochroman-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pivaloyl chloride; dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 - 50 °C / Large scale 2: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale 3: sodium phosphate; sulfuryl dichloride / ethyl acetate / 10 °C / Large scale View Scheme | |
Multi-step reaction with 4 steps 1: thionyl chloride / toluene / 65 - 70 °C 2: pyridine / dichloromethane / 6 h / 0 - 25 °C 3: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale 4: sodium phosphate; sulfuryl dichloride / ethyl acetate / 10 °C / Large scale View Scheme | |
Multi-step reaction with 3 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.33 h / 20 - 25 °C / Large scale 1.2: 20 - 50 °C / Large scale 2.1: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale 3.1: sulfuryl dichloride; sodium phosphate / ethyl acetate / 10 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: thionyl chloride / toluene / 65 - 70 °C 2: pyridine / dichloromethane / 6 h / 0 - 25 °C 3: trifluoroacetic acid / acetonitrile / 7 h / 50 - 55 °C / Large scale 4: sulfuryl dichloride; sodium phosphate / ethyl acetate / 10 - 20 °C View Scheme |
Conditions | Yield |
---|---|
With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 50℃; Large scale; | |
Stage #1: cycl-isopropylidene malonate; (S)-6-fluorochroman-2-carboxylic acid With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 25℃; for 0.333333h; Large scale; Stage #2: With pivaloyl chloride In acetonitrile at 20 - 50℃; Large scale; |
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide; toluene at 80℃; for 6h; | 1.7 g |
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide at 140℃; for 4.5h; | 1.7 g |
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