2H-1-Benzopyran-2-carboxylic acid, 6-fluoro-3,4-dihydro-, (2S)-

Base Information

• Chemical Name: 2H-1-Benzopyran-2-carboxylic acid, 6-fluoro-3,4-dihydro-, (2S)-
• CAS No.: 129101-36-6
• Molecular Formula: C10H9FO3
• Molecular Weight: 196.178
• Hs Code.: 2932990090
• Mol file: 129101-36-6.mol

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;

Chemical Property of 2H-1-Benzopyran-2-carboxylic acid, 6-fluoro-3,4-dihydro-, (2S)-

Chemical Property:

• Boiling Point: 358.0±42.0 °C(Predicted)
• PKA: 3.05±0.20(Predicted)
• PSA: 46.53000
• Density: 1.364±0.06 g/cm3(Predicted)
• LogP: 1.60390

Purity/Quality:

99.9% ^*data from raw suppliers

(S)-6-Fluorochromane-2-carboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2H-1-Benzopyran-2-carboxylic acid, 6-fluoro-3,4-dihydro-, (2S)-

There total 15 articles about 2H-1-Benzopyran-2-carboxylic acid, 6-fluoro-3,4-dihydro-, (2S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

6-fluoro-4H-chromene-2-carboxylic acid → (S)-6-fluorochroman-2-carboxylic acid (129101-36-6,129050-20-0)

Guidance literature:

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

DOI:10.1002/anie.201301341

Reference yield: 95.0%

(S)-methyl 6-fluorochroman-2-carboxylate (1219915-01-1) → (S)-6-fluorochroman-2-carboxylic acid (129101-36-6,129050-20-0)

Guidance literature:

(S)-methyl 6-fluorochroman-2-carboxylate; With sodium hydroxide; In tetrahydrofuran; methanol; water; at 0 - 20 ℃; for 6h; Schlenk technique;

With hydrogenchloride; In tetrahydrofuran; methanol; water; Schlenk technique;

DOI:10.1002/anie.201209455

Reference yield:

5-fluoro-2-hydroxybenzaldehyde (347-54-6) → (S)-6-fluorochroman-2-carboxylic acid (129101-36-6,129050-20-0)

Guidance literature:

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

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; tetrakis(actonitrile)copper(I) hexafluorophosphate; palladium 10% on activated carbon; C₃₅H₃₀N₂O₂; potassium tert-butylate; hydrogen; iodine; sodium hydride; potassium carbonate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; triethylamine; Methanesulfonyl azide; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1002/anie.201209455

upstream raw materials:

5-fluoro-2-hydroxybenzaldehyde

2-(benzyloxy)-5-fluorobenzaldehyde

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

6-fluoro-3,4-dihydro-2H-benzopyran-2-carboxylic acid ethyl ester

Downstream raw materials:

(+)-(S)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carbonyl chloride

Refernces

• 1、 Song, Song,Zhu, Shou-Fei,Pu, Liu-Yang,Zhou, Qi-Lin. "Iridium-catalyzed enantioselective hydrogenation of unsaturated heterocyclic acids". supporting information. p. 6072 - 6075. Retrieved 2013/07/05.