1-(2-Hydroxy-3-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4,6-dimethoxyphenyl)ethan-1-one

Base Information

• Chemical Name: 1-(2-Hydroxy-3-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4,6-dimethoxyphenyl)ethan-1-one
• CAS No.: 113225-21-1
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362
• European Community (EC) Number: 601-245-1
• DSSTox Substance ID: DTXSID601126316
• Mol file: 113225-21-1.mol

Synonyms:113225-21-1;1-(2-Hydroxy-3-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4,6-dimethoxyphenyl)ethan-1-one;SCHEMBL2512372;DTXSID601126316;1-[2-Hydroxy-3-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4,6-dimethoxyphenyl]ethanone

Chemical Property of 1-(2-Hydroxy-3-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4,6-dimethoxyphenyl)ethan-1-one

Chemical Property:

• Vapor Pressure: 1.6E-08mmHg at 25°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 391

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C1=C(C=C(C(=C1O)C2CCN(CC2O)C)OC)OC
• Isomeric SMILES: CC(=O)C1=C(C=C(C(=C1O)[C@H]2CCN(C[C@H]2O)C)OC)OC

Technology Process of 1-(2-Hydroxy-3-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4,6-dimethoxyphenyl)ethan-1-one

There total 5 articles about 1-(2-Hydroxy-3-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4,6-dimethoxyphenyl)ethan-1-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: 82.6%

acetic anhydride (108-24-7) + (3S,4R)-1-methyl-4-(2,4,6-trimethoxyphenyl)-3-piperidinol (113225-19-7,234771-34-7) → (3S,4R)-4-(3-acetyl-2-hydroxy-4,6-dimethoxyphenyl)-1-methyl-3-piperidinol (113225-21-1)

Guidance literature:

acetic anhydride; (3S,4R)-1-methyl-4-(2,4,6-trimethoxyphenyl)-3-piperidinol; With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃;

In methanol; for 48h; Further stages.;

DOI:10.1021/jm000231g

Reference yield: 73.0%

acetic anhydride (108-24-7) + cis-3-Hydroxy-4-(2,4,6-trimethoxyphenyl)-1-methylpiperidine (113225-08-4,113225-12-0,113225-18-6,113225-19-7,117955-02-9,234771-34-7) → (-)-cis-4-(3-acetyl-4,6-dimethoxy-2-hydroxy)phenyl-1-methyl-3-piperidinol (113225-14-2,113225-21-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4020(01)90352-7

Reference yield:

(+)-1-Methyl-4-(2,4,6-trimethoxyphenyl)-piperidin-3-one (113225-10-8) → (3S,4R)-4-(3-acetyl-2-hydroxy-4,6-dimethoxyphenyl)-1-methyl-3-piperidinol (113225-21-1)

Guidance literature:

Multi-step reaction with 3 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

With O,O'-dibenzoyl-D-tartaric acid; boron trifluoride diethyl etherate; diisobutylaluminium hydride; In methanol; dichloromethane; 1.1: salt formation / 2.1: Reduction / 3.1: Acetylation / 3.2: Hydrolysis;

DOI:10.1021/jm000231g

upstream raw materials:

acetic anhydride

cis-3-Hydroxy-4-(2,4,6-trimethoxyphenyl)-1-methylpiperidine

(3S,4R)-1-methyl-4-(2,4,6-trimethoxyphenyl)-3-piperidinol

(+)-1-Methyl-4-(2,4,6-trimethoxyphenyl)-piperidin-3-one

Downstream raw materials:

(+)-cisa-5,7-dihydroxy-methyl-8-<4-(3-hydroxy-1-methyl)piperidinyl>-4H-1-benzopyran-4-one

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

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