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129101-36-6

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Basic Information
CAS No.: 129101-36-6
Name: 2H-1-Benzopyran-2-carboxylic acid, 6-fluoro-3,4-dihydro-, (2S)-
Article Data: 3
Molecular Structure:
Molecular Structure of 129101-36-6 (2H-1-Benzopyran-2-carboxylic acid, 6-fluoro-3,4-dihydro-, (2S)-)
Formula: C10H9FO3
Molecular Weight: 196.178
Synonyms: (S)-5-(aminomethyl)-2-pyrrolidinone;(S)-5-Aminomethyl-pyrrolidin-2-one;(+)-(S)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid;2-Pyrrolidinone,5-(aminomethyl)-,(5S);(S)-5-(aminomethyl)-2-pyrrolidone;(S)-6-fluorochroman-2-carboxylic acid;
Density: 1.364±0.06 g/cm3(Predicted)
Boiling Point: 358.0±42.0 °C(Predicted)
PSA: 46.53000
LogP: 1.60390
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Synthetic route

6-fluoro-4H-chromene-2-carboxylic acid

129101-36-6

(S)-6-fluorochroman-2-carboxylic acid

Conditions
ConditionsYield
With C63H78IrNOP(2+)*C32H12BF24(1-); hydrogen; caesium carbonate In methanol at 60℃; under 4560.31 Torr; for 12h; Autoclave; enantioselective reaction;99%
1219915-01-1

(S)-methyl 6-fluorochroman-2-carboxylate

129101-36-6

(S)-6-fluorochroman-2-carboxylic acid

Conditions
ConditionsYield
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%
347-54-6

5-fluoro-2-hydroxybenzaldehyde

129101-36-6

(S)-6-fluorochroman-2-carboxylic acid

Conditions
ConditionsYield
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

2-[2-(benzyloxy)-5-fluorophenyl]ethan-1-ol

129101-36-6

(S)-6-fluorochroman-2-carboxylic acid

Conditions
ConditionsYield
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

C16H15FO2

129101-36-6

(S)-6-fluorochroman-2-carboxylic acid

Conditions
ConditionsYield
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

C15H14FIO

129101-36-6

(S)-6-fluorochroman-2-carboxylic acid

Conditions
ConditionsYield
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

C13H15FO4

129101-36-6

(S)-6-fluorochroman-2-carboxylic acid

Conditions
ConditionsYield
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

methyl 2-diazo-4-(5-fluoro-2-hydroxyphenyl)butanoate

129101-36-6

(S)-6-fluorochroman-2-carboxylic acid

Conditions
ConditionsYield
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
312314-37-7

2-(benzyloxy)-5-fluorobenzaldehyde

129101-36-6

(S)-6-fluorochroman-2-carboxylic acid

Conditions
ConditionsYield
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

2-(2-(benzyloxy)-5-fluorophenyl)acetaldehyde

129101-36-6

(S)-6-fluorochroman-2-carboxylic acid

Conditions
ConditionsYield
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
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