3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-N-methyl-acrylamide

Base Information

• Chemical Name: 3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-N-methyl-acrylamide
• CAS No.: 791814-54-5
• Molecular Formula: C₂₅H₂₉NO₆
• Molecular Weight: 439.508

Synonyms:3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-N-methyl-acrylamide

Chemical Property of 3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-N-methyl-acrylamide

Chemical Property:

Purity/Quality:

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Technology Process of 3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-N-methyl-acrylamide

There total 13 articles about 3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-N-methyl-acrylamide 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: 79.0%

diethyl <(N-methylcarbamoyl)methyl>phosphonate (72563-39-4) + 4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde (791814-46-5) → 3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-N-methyl-acrylamide (791814-54-5)

Guidance literature:

With sodium hydroxide; tetrahexylammonium iodide; In dichloromethane;

DOI:10.1021/jo049157q

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-N-methyl-acrylamide (791814-54-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 72 percent / camphorsulfonic acid monohydrate / CH₂Cl₂ / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.2: trimethyl borate / tetrahydrofuran; hexane / 1.25 h / cooling

3.1: 77 percent / Pd(OAc)2; Ph₃P; aq. NaHCO₃ / dioxane / 12 h / Heating

4.1: toluene / 2 h / Heating

5.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / cooling

5.2: trimethylborate / tetrahydrofuran; hexane / 1.25 h / cooling

5.3: 1.70 g / hydrogen peroxide; AcOH / tetrahydrofuran; hexane / 16 h / 20 °C

6.1: 54 percent / aq. HCl / tetrahydrofuran / 0.25 h / Heating

7.1: 88 percent / K₂CO₃ / tetrahydrofuran / 3 h / Heating

8.1: 79 percent / tetrahexylammonium iodide; aq. NaOH / CH₂Cl₂

With hydrogenchloride; palladium diacetate; sodium hydroxide; n-butyllithium; camphor-10-sulfonic acid; sodium hydrogencarbonate; tetrahexylammonium iodide; potassium carbonate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; toluene; 3.1: Suzuki coupling;

DOI:10.1021/jo049157q

Reference yield:

2-bromophenylethyl alcohol (1074-16-4) → 3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-N-methyl-acrylamide (791814-54-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 72 percent / camphorsulfonic acid monohydrate / CH₂Cl₂ / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.2: trimethyl borate / tetrahydrofuran; hexane / 1.25 h / cooling

3.1: 77 percent / Pd(OAc)2; Ph₃P; aq. NaHCO₃ / dioxane / 12 h / Heating

4.1: toluene / 2 h / Heating

5.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / cooling

5.2: trimethylborate / tetrahydrofuran; hexane / 1.25 h / cooling

5.3: 1.70 g / hydrogen peroxide; AcOH / tetrahydrofuran; hexane / 16 h / 20 °C

6.1: 54 percent / aq. HCl / tetrahydrofuran / 0.25 h / Heating

7.1: 88 percent / K₂CO₃ / tetrahydrofuran / 3 h / Heating

8.1: 79 percent / tetrahexylammonium iodide; aq. NaOH / CH₂Cl₂

With hydrogenchloride; palladium diacetate; sodium hydroxide; n-butyllithium; camphor-10-sulfonic acid; sodium hydrogencarbonate; tetrahexylammonium iodide; potassium carbonate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; toluene; 3.1: Suzuki coupling;

DOI:10.1021/jo049157q

upstream raw materials:

diethyl <(N-methylcarbamoyl)methyl>phosphonate

4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde

3,4-dihydro-2H-pyran

piperonal

Downstream raw materials:

[3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-propyl]-methyl-carbamic acid tert-butyl ester

methanesulfonic acid 2-(2-{6-[3-(tert-butoxycarbonyl-methyl-amino)-propyl]-7-methoxy-benzo[1,3]dioxol-5-yl}-phenyl)-ethyl ester

[3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-propyl]-methyl-amine

(3-{6-[2-(2-hydroxy-ethyl)-phenyl]-4-methoxy-benzo[1,3]dioxol-5-yl}-propyl)-methyl-carbamic acid tert-butyl ester

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