(±)-α-N-demethyl hydrastine

Base Information

Chemical Name:(±)-α-N-demethyl hydrastine
CAS No.:68780-76-7
Molecular Formula:C₂₀H₁₉NO₆
Molecular Weight:369.374
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (±)-α-N-demethyl hydrastine

Chemical Property:

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Technology Process of (±)-α-N-demethyl hydrastine

There total 13 articles about (±)-α-N-demethyl 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%

: 68753-57-1
3-[1,3]dioxolo[4,5-g]isoquinolin-5-yl-6,7-dimethoxy-3H-isobenzofuran-1-one

: 68780-76-7
(±)-α-N-demethyl hydrastine

: 66408-36-4
(+/-)-β-Norhydrastin

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

: 68780-76-7
(±)-α-N-demethyl hydrastine

: 66408-36-4
(+/-)-β-Norhydrastin

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

Reference yield:

: 1521-38-6
2,3-dimethoxybenzoic acid

: 68780-76-7
(±)-α-N-demethyl hydrastine

: 66408-36-4
(+/-)-β-Norhydrastin

Guidance literature:: Multi-step reaction with 8 steps

1.1: palladium diacetate; dipotassium hydrogenphosphate / 8 h / 96 °C

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 4 h / Reflux

3.1: water; potassium hydroxide / 4 h / 40 °C

3.2: 1 h / 5 °C / pH 1 - 2

4.1: thionyl chloride / 4.5 h / 0 - 20 °C

5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / 0 - 20 °C

5.2: 0.5 h / 0 - 20 °C

6.1: acetic acid; palladium diacetate; silver(I) acetate / 1.5 h / 117 °C / Inert atmosphere

7.1: oxone||potassium monopersulfate triple salt; sodium hydrogencarbonate / water; dichloromethane; acetone / 0 °C

8.1: trifluoroacetic acid / dichloromethane / 3 h / 0 °C

8.2: 3 h / 0 - 20 °C

With dipotassium hydrogenphosphate; N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); oxone||potassium monopersulfate triple salt; water; silver(I) acetate; palladium diacetate; potassium hexamethylsilazane; sodium hydrogencarbonate; acetic acid; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetone; 5.1: |Wittig Olefination / 5.2: |Wittig Olefination / 6.1: |Heck Reaction;
DOI:10.1021/acs.orglett.9b02715