(+/-)-Nor-β-hydrastine

Base Information

• Chemical Name: (+/-)-Nor-β-hydrastine
• CAS No.: 66408-36-4
• Molecular Formula: C₂₀H₁₉NO₆
• Molecular Weight: 369.374
• Mol file: 66408-36-4.mol

Synonyms:

Chemical Property of (+/-)-Nor-β-hydrastine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

(+/-)-Nor-β-hydrastine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: GABAergic receptor-binding phthalideisoquinoline alkaloids GABAergic receptor-binding phthalideisoquinoline alkaloids.

Technology Process of (+/-)-Nor-β-hydrastine

There total 26 articles about (+/-)-Nor-β-hydrastine 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: 35.0%

3-[1,3]dioxolo[4,5-g]isoquinolin-5-yl-6,7-dimethoxy-3H-isobenzofuran-1-one (68753-57-1) → (±)-α-N-demethyl hydrastine (68780-76-7) + (+/-)-β-Norhydrastin (66408-36-4)

Guidance literature:

With perchloric acid; hydrogen; platinum(IV) oxide; In ethanol; for 10h; under 1810.02 Torr;

DOI:10.1021/jo00173a019

Reference yield:

9,10,13a-trimethoxy-2,3-(methylenedioxy)-8,13-dioxo-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine (71733-96-5,95585-80-1) → (+/-)-β-Norhydrastin (66408-36-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 15 percent / 0.33 h / 175 °C / 15 Torr

2: 35 percent / H₂, 70percent HClO₄ / Adams catalyst / ethanol / 10 h / 1810.02 Torr

With perchloric acid; hydrogen; platinum(IV) oxide; In ethanol;

DOI:10.1021/jo00173a019

Reference yield:

methyl 6-(3-(6-(2-((tert-butoxycarbonyl)amino)ethyl)benzo[d][1,3]dioxol-5-yl)oxiran-2-yl)-2,3-dimethoxybenzoate → (±)-α-N-demethyl hydrastine (68780-76-7) + (+/-)-β-Norhydrastin (66408-36-4)

Guidance literature:

methyl 6-(3-(6-(2-((tert-butoxycarbonyl)amino)ethyl)benzo[d][1,3]dioxol-5-yl)oxiran-2-yl)-2,3-dimethoxybenzoate; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 3h;

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 3h; diastereoselective reaction;

DOI:10.1021/acs.orglett.9b02715

upstream raw materials:

2,3-dimethoxy-6-(5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline-5-carbonyl)-benzoic acid methyl ester; hydrochloride

(RS)-6-[hydroxy-((SR)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-methyl]-2,3-dimethoxy-benzoic acid

3-[1,3]dioxolo[4,5-g]isoquinolin-5-yl-6,7-dimethoxy-3H-isobenzofuran-1-one

2-bromo-3,4-dimethoxybenzylaldehyde

Refernces

• 1、 Seebach,Dieter,Huber, Isabelle M. P.,Syfrig, Max A.. "Diastereoselektive Hydroxyalkylierungen in 1-Stellung von Tetrahydroisochinolinen und Synthese von Aporphin-, Protoberberin- und Phthalid-Alkaloiden". . p. 1357 - 1379. Retrieved 2007/10/02.