(3S,4R)-2-(2-chlorophenyl)-8-(3-hydroxy-1-methyl-4-piperidinyl)-5,7-dimethoxy-4H-1-benzopyran-4-one

Base Information

Chemical Name:(3S,4R)-2-(2-chlorophenyl)-8-(3-hydroxy-1-methyl-4-piperidinyl)-5,7-dimethoxy-4H-1-benzopyran-4-one
CAS No.:199589-13-4
Molecular Formula:C₂₃H₂₄ClNO₆
Molecular Weight:445.9
Hs Code.:

Synonyms:(3S,4R)-2-(2-chlorophenyl)-8-(3-hydroxy-1-methyl-4-piperidinyl)-5,7-dimethoxy-4H-1-benzopyran-4-one

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Chemical Property of (3S,4R)-2-(2-chlorophenyl)-8-(3-hydroxy-1-methyl-4-piperidinyl)-5,7-dimethoxy-4H-1-benzopyran-4-one

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Technology Process of (3S,4R)-2-(2-chlorophenyl)-8-(3-hydroxy-1-methyl-4-piperidinyl)-5,7-dimethoxy-4H-1-benzopyran-4-one

There total 6 articles about (3S,4R)-2-(2-chlorophenyl)-8-(3-hydroxy-1-methyl-4-piperidinyl)-5,7-dimethoxy-4H-1-benzopyran-4-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: 76.0%

: 3046-25-1
o-chlorophenol, potassium salt

: 199589-15-6
(3S,4R)-2-(ethylthio)-8-(3-hydroxy-1-methyl-4-piperidyl)-5,7-dimethoxy-4H-1-benzopyran-4-one

: 199589-13-4
(3S,4R)-2-(2-chlorophenyl)-8-(3-hydroxy-1-methyl-4-piperidinyl)-5,7-dimethoxy-4H-1-benzopyran-4-one

Guidance literature:: (3S,4R)-2-(ethylthio)-8-(3-hydroxy-1-methyl-4-piperidyl)-5,7-dimethoxy-4H-1-benzopyran-4-one; With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;

o-chlorophenol, potassium salt; In tetrahydrofuran; at 0 ℃; for 1h; Further stages.;
DOI:10.1021/jm000231g

Reference yield:

: 113225-10-8
(+)-1-Methyl-4-(2,4,6-trimethoxyphenyl)-piperidin-3-one

: 199589-13-4
(3S,4R)-2-(2-chlorophenyl)-8-(3-hydroxy-1-methyl-4-piperidinyl)-5,7-dimethoxy-4H-1-benzopyran-4-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 76 percent / dibenzoyl-D-tartaric acid / methanol / 25 - 85 °C

2.1: 56 percent / DIBAL-H / CH₂Cl₂ / 3.5 h / -78 °C

3.1: BF₃*Et₂O / CH₂Cl₂ / 20 °C

3.2: 82.6 percent / 20percent aq. KOH / methanol / 48 h

4.1: LHMDS / tetrahydrofuran / 2 h / 20 °C

5.1: Cs₂CO₃ / dimethylformamide / 18 h / 20 °C

6.1: CF₃CO₂H; m-CPBA / CH₂Cl₂ / 1 h / 0 °C

6.2: 76 percent / tetrahydrofuran / 1 h / 0 °C

With O,O'-dibenzoyl-D-tartaric acid; boron trifluoride diethyl etherate; diisobutylaluminium hydride; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: salt formation / 2.1: Reduction / 3.1: Acetylation / 3.2: Hydrolysis / 4.1: Cyclization / 5.1: Alkylation / 6.1: Oxidation / 6.2: Substitution;
DOI:10.1021/jm000231g

Reference yield:

: 205506-14-5
(R)-1-methyl-4-(2,4,6-trimethoxyphenyl)-3-piperidinone

: 199589-13-4
(3S,4R)-2-(2-chlorophenyl)-8-(3-hydroxy-1-methyl-4-piperidinyl)-5,7-dimethoxy-4H-1-benzopyran-4-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 56 percent / DIBAL-H / CH₂Cl₂ / 3.5 h / -78 °C

2.1: BF₃*Et₂O / CH₂Cl₂ / 20 °C

2.2: 82.6 percent / 20percent aq. KOH / methanol / 48 h

3.1: LHMDS / tetrahydrofuran / 2 h / 20 °C

4.1: Cs₂CO₃ / dimethylformamide / 18 h / 20 °C

5.1: CF₃CO₂H; m-CPBA / CH₂Cl₂ / 1 h / 0 °C

5.2: 76 percent / tetrahydrofuran / 1 h / 0 °C

With boron trifluoride diethyl etherate; diisobutylaluminium hydride; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Acetylation / 2.2: Hydrolysis / 3.1: Cyclization / 4.1: Alkylation / 5.1: Oxidation / 5.2: Substitution;
DOI:10.1021/jm000231g