(1R,3R)-2-benzyl-5-(5-hydroxy-4-methoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol

Base Information

• Chemical Name: (1R,3R)-2-benzyl-5-(5-hydroxy-4-methoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
• CAS No.: 146471-75-2
• Molecular Formula: C₂₃H₂₅NO₃
• Molecular Weight: 363.456
• Mol file: 146471-75-2.mol

Synonyms:8-Isoquinolinol,1,2,3,4-tetrahydro-5-(5-hydroxy-4-methoxy-2-methyl-1-naphthalenyl)-1,3-dimethyl-,stereoisomer; (+)-Dioncophylline C; Dioncophylline C

Chemical Property of (1R,3R)-2-benzyl-5-(5-hydroxy-4-methoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 575.553°C at 760 mmHg
• Flash Point: 301.884°C
• Density: 1.187g/cm³

Purity/Quality:

≥98% （HPLC） ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R)-2-benzyl-5-(5-hydroxy-4-methoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol

There total 17 articles about (1R,3R)-2-benzyl-5-(5-hydroxy-4-methoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol 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:

(1R,3R)-2-Benzyl-5-(5-hydroxy-4-methoxy-2-methyl-naphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-8-ol → dioncophylline C (146471-75-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr;

DOI:10.1016/S0040-4020(97)10301-5

Reference yield:

(1R,3R)-2-Benzyl-6-methoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-8-ol → dioncophylline C (146471-75-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 87 percent / aq. NaOH; Bu₃N*HCl / CH₂Cl₂ / 168 h / 20 °C

2.1: 68 percent / sodium thioisopropylate / dimethylformamide / 3 h / Heating

3.1: 71 percent / N,N-diisopropylethylamine; N,N-dimethylaminopyridine / CH₂Cl₂

4.1: 69 percent / NaOAc / (PPh₃)2PdCl₂ / N,N-dimethyl-acetamide / 100 °C

5.1: 117 mg / LiAlH₄ / tetrahydrofuran / 0.08 h

6.1: triphenylphosphine; 1,2-dibromotetrachloroethane / CH₂Cl₂ / 0.17 h

6.2: 95 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

7.1: thallium ethanolate / CH₂Cl₂ / 0.5 h / 20 °C

7.2: CH₂Cl₂ / 0.08 h

8.1: 33.0 mg / dppp; n-Bu₃N; formic acid / (PPh₃)2PdCl₂ / dimethylformamide / 2.5 h / 100 °C

9.1: boron trifluoride / CH₂Cl₂; hexane / 5 h / -40 - -15 °C

10.1: 11.4 mg / H₂ / Pd/C / methanol / 760 Torr

With dmap; sodium hydroxide; lithium aluminium tetrahydride; formic acid; tributyl-amine; 1,2-dibromo-1,1,2,2-tetrachloroethane; sodium thioisopropylate; 1,3-bis-(diphenylphosphino)propane; boron trifluoride; hydrogen; sodium acetate; thallium (I) ethoxide; tri-n-butylamine hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: demethylation / 3.1: Esterification / 4.1: Cyclization / 5.1: Reduction / 6.1: halogenation / 6.2: Reduction / 7.1: Metallation / 7.2: Esterification / 8.1: Reduction / 9.1: dealkylation / 10.1: Hydrogenolysis;

DOI:10.1016/S0040-4020(97)10301-5

Reference yield:

Ethyl 8-bromo-5-isopropoxy-4-methoxy-2-naphthoate (162147-18-4) → dioncophylline C (146471-75-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: H₂; Et₃N / Pd/C / methanol / 15 h / 3750.3 Torr

2.1: 7.77 g / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

3.1: 95 percent / NaOAc; N(n-Bu)4Br₃ / CH₂Cl₂ / 1 h / 0 °C

4.1: 90 percent / MnO₂ / CH₂Cl₂ / 1.5 h / Heating

5.1: 98 percent / NaClO₂; sulphamic acid; NaOAc / acetic acid; H₂O; dioxane / 4 h / 20 °C

6.1: DMF; oxalyl chloride / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 71 percent / N,N-diisopropylethylamine; N,N-dimethylaminopyridine / CH₂Cl₂

8.1: 69 percent / NaOAc / (PPh₃)2PdCl₂ / N,N-dimethyl-acetamide / 100 °C

9.1: 117 mg / LiAlH₄ / tetrahydrofuran / 0.08 h

10.1: triphenylphosphine; 1,2-dibromotetrachloroethane / CH₂Cl₂ / 0.17 h

10.2: 95 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

11.1: thallium ethanolate / CH₂Cl₂ / 0.5 h / 20 °C

11.2: CH₂Cl₂ / 0.08 h

12.1: 33.0 mg / dppp; n-Bu₃N; formic acid / (PPh₃)2PdCl₂ / dimethylformamide / 2.5 h / 100 °C

13.1: boron trifluoride / CH₂Cl₂; hexane / 5 h / -40 - -15 °C

14.1: 11.4 mg / H₂ / Pd/C / methanol / 760 Torr

With dmap; manganese(IV) oxide; sodium chlorite; lithium aluminium tetrahydride; formic acid; oxalyl dichloride; tributyl-amine; 1,2-dibromo-1,1,2,2-tetrachloroethane; 1,3-bis-(diphenylphosphino)propane; aminosulfonic acid; boron trifluoride; hydrogen; sodium acetate; thallium (I) ethoxide; tetra-N-butylammonium tribromide; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; N,N-dimethyl acetamide; water; acetic acid; N,N-dimethyl-formamide; 1.1: Hydrogenation / 2.1: Reduction / 3.1: Bromination / 4.1: Oxidation / 5.1: Oxidation / 6.1: Chlorination / 7.1: Esterification / 8.1: Cyclization / 9.1: Reduction / 10.1: halogenation / 10.2: Reduction / 11.1: Metallation / 11.2: Esterification / 12.1: Reduction / 13.1: dealkylation / 14.1: Hydrogenolysis;

DOI:10.1016/S0040-4020(97)10301-5

upstream raw materials:

Ethyl 8-bromo-5-isopropoxy-4-methoxy-2-naphthoate

(1R,3R)-N-benzyl-6-hydroxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

1-bromo-5-isopropoxy-4-methoxynaphthalene-2-carbaldehyde

2-hydroxymethyl-5-isopropoxy-4-methoxynaphthalene

Refernces