(4R,6S)-6-[2-(4-Fluoro-phenyl)-4-methyl-quinolin-3-yloxymethyl]-4-hydroxy-tetrahydro-pyran-2-one

Base Information

Chemical Name:(4R,6S)-6-[2-(4-Fluoro-phenyl)-4-methyl-quinolin-3-yloxymethyl]-4-hydroxy-tetrahydro-pyran-2-one
CAS No.:136006-79-6
Molecular Formula:C₂₂H₂₀FNO₄
Molecular Weight:381.404
Hs Code.:

Synonyms:(4R,6S)-6-[2-(4-Fluoro-phenyl)-4-methyl-quinolin-3-yloxymethyl]-4-hydroxy-tetrahydro-pyran-2-one

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Chemical Property of (4R,6S)-6-[2-(4-Fluoro-phenyl)-4-methyl-quinolin-3-yloxymethyl]-4-hydroxy-tetrahydro-pyran-2-one

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Technology Process of (4R,6S)-6-[2-(4-Fluoro-phenyl)-4-methyl-quinolin-3-yloxymethyl]-4-hydroxy-tetrahydro-pyran-2-one

There total 17 articles about (4R,6S)-6-[2-(4-Fluoro-phenyl)-4-methyl-quinolin-3-yloxymethyl]-4-hydroxy-tetrahydro-pyran-2-one 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: 82.0%

: 136007-68-6
(4R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-fluoro-phenyl)-4-methyl-quinolin-3-yloxymethyl]-tetrahydro-pyran-2-one

: 136006-79-6
(4R,6S)-6-[2-(4-Fluoro-phenyl)-4-methyl-quinolin-3-yloxymethyl]-4-hydroxy-tetrahydro-pyran-2-one

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1021/jm00114a004

Reference yield:

: 136007-11-9
2,3-dichloro-6-(cyclohexylidenefluoromethyl)phenol

: 136006-79-6
(4R,6S)-6-[2-(4-Fluoro-phenyl)-4-methyl-quinolin-3-yloxymethyl]-4-hydroxy-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 11 steps

1: K₂CO₃, hydroquinone / dimethylsulfoxide / 1 h / 40 °C

2: glacial acetic acid / tetrahydrofuran / 72 h / Heating

3: CrO₃, pyridine, Celite / CH₂Cl₂ / 1 h / 20 - 25 °C

4: 75 percent / glacial acetic acid, tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C

5: 1N NaOH / ethanol / 1 h / 20 - 25 °C

6: 69 percent / LiAlH₄ / diethyl ether / 2 h / Heating

7: 69 percent / conc. HCl, H₂ / 10percent Pd/c / acetic acid / 24 h / 750.06 Torr

8: K₂CO₃, hydroquinone / dimethylsulfoxide / 2 h / 50 °C

9: CF₃COOH / tetrahydrofuran; H₂O / 4 h / 60 °C

10: tetra-n-butylammonium iodide, N-iodosuccinimide / CH₂Cl₂ / 20 h / Ambient temperature

11: 82 percent / glacial acetic acid, tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; Celite; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; hydroquinone; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetic acid; dimethyl sulfoxide;
DOI:10.1021/jm00114a004

Reference yield:

: 136007-08-4
2,4-dichloro-6-(cyclohexylcarbonyl)phenol

: 136006-79-6
(4R,6S)-6-[2-(4-Fluoro-phenyl)-4-methyl-quinolin-3-yloxymethyl]-4-hydroxy-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 12 steps

1: 47 percent / Et₂NSF₃ / toluene / 2 h / 25 °C

2: K₂CO₃, hydroquinone / dimethylsulfoxide / 1 h / 40 °C

3: glacial acetic acid / tetrahydrofuran / 72 h / Heating

4: CrO₃, pyridine, Celite / CH₂Cl₂ / 1 h / 20 - 25 °C

5: 75 percent / glacial acetic acid, tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C

6: 1N NaOH / ethanol / 1 h / 20 - 25 °C

7: 69 percent / LiAlH₄ / diethyl ether / 2 h / Heating

8: 69 percent / conc. HCl, H₂ / 10percent Pd/c / acetic acid / 24 h / 750.06 Torr

9: K₂CO₃, hydroquinone / dimethylsulfoxide / 2 h / 50 °C

10: CF₃COOH / tetrahydrofuran; H₂O / 4 h / 60 °C

11: tetra-n-butylammonium iodide, N-iodosuccinimide / CH₂Cl₂ / 20 h / Ambient temperature

12: 82 percent / glacial acetic acid, tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; diethylamino-sulfur trifluoride; Celite; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; hydroquinone; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; toluene;
DOI:10.1021/jm00114a004