(±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline

Base Information

• Chemical Name: (±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline
• CAS No.: 79043-20-2
• Molecular Formula: C₂₁H₂₅NO₇
• Molecular Weight: 403.432
• Mol file: 79043-20-2.mol

Synonyms:(±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline

Chemical Property of (±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline

There total 15 articles about (±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline 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: 93.0%

C42H43NO7 → (±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline (79043-20-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 40h; Schlenk technique;

DOI:10.1021/acs.orglett.0c00577

Reference yield:

methyl galloate (99-24-1) → (±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline (79043-20-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: triethylamine / 2.25 h / 0 - 20 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 6.5 h / 0 - 50 °C

3.1: potassium carbonate / water; methanol / 1.5 h / 20 °C

4.1: potassium carbonate / acetone / 0.25 h / 20 °C

4.2: 2 h / Reflux

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 - 20 °C / Inert atmosphere

6.1: thionyl chloride / dichloromethane / 2.5 h / 20 °C

7.1: N,N-dimethyl-formamide / 17 h / 20 °C / Inert atmosphere

8.1: potassium hydroxide / ethanol; water / 20 h / Reflux

9.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere

10.1: trichlorophosphate / acetonitrile / 2 h / 0 °C / Reflux; Inert atmosphere

10.2: 19 h / 20 °C

11.1: potassium carbonate / dichloromethane / 16 h / 20 °C

12.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 40 h / 20 °C / Schlenk technique

With lithium aluminium tetrahydride; thionyl chloride; palladium 10% on activated carbon; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/acs.orglett.0c00577

Reference yield:

methyl 3,5-diacetoxy-4-methoxy benzoate (13089-97-9) → (±)-N-(ethoxycarbonyl)-5'-hydroxynorreticuline (79043-20-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium carbonate / water; methanol / 1.5 h / 20 °C

2.1: potassium carbonate / acetone / 0.25 h / 20 °C

2.2: 2 h / Reflux

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 - 20 °C / Inert atmosphere

4.1: thionyl chloride / dichloromethane / 2.5 h / 20 °C

5.1: N,N-dimethyl-formamide / 17 h / 20 °C / Inert atmosphere

6.1: potassium hydroxide / ethanol; water / 20 h / Reflux

7.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere

8.1: trichlorophosphate / acetonitrile / 2 h / 0 °C / Reflux; Inert atmosphere

8.2: 19 h / 20 °C

9.1: potassium carbonate / dichloromethane / 16 h / 20 °C

10.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 40 h / 20 °C / Schlenk technique

With lithium aluminium tetrahydride; thionyl chloride; palladium 10% on activated carbon; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; potassium hydroxide; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/acs.orglett.0c00577

upstream raw materials:

3-Methoxytyramine

2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetic acid

methyl galloate

3,4,5-triacetoxy-benzoic acid methyl ester