[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

Base Information

• Chemical Name: [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
• CAS No.: 791814-62-5
• Molecular Formula: C₃₀H₄₁NO₇
• Molecular Weight: 527.658

Synonyms:[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

Chemical Property of [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

Chemical Property:

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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)-propyl]-methyl-carbamic acid tert-butyl ester

There total 16 articles about [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 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:

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)-propyl]-methyl-carbamic acid tert-butyl ester (791814-62-5)

Guidance literature:

Multi-step reaction with 11 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

9.1: 99 percent / hydrogen / Raney nickel / methanol / 24 h

10.1: LiAlH₄ / tetrahydrofuran / 2 h / Heating

11.1: 0.50 g / Et₃N / CH₂Cl₂ / 1 h

With hydrogenchloride; palladium diacetate; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; hydrogen; sodium hydrogencarbonate; tetrahexylammonium iodide; potassium carbonate; triethylamine; triphenylphosphine; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; 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)-propyl]-methyl-carbamic acid tert-butyl ester (791814-62-5)

Guidance literature:

Multi-step reaction with 11 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

9.1: 99 percent / hydrogen / Raney nickel / methanol / 24 h

10.1: LiAlH₄ / tetrahydrofuran / 2 h / Heating

11.1: 0.50 g / Et₃N / CH₂Cl₂ / 1 h

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

DOI:10.1021/jo049157q

Reference yield:

2-(2-bromophenyl)ethyl tetrahydro-2H-pyran-2-yl ether (143888-88-4) → [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 (791814-62-5)

Guidance literature:

Multi-step reaction with 10 steps

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

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

2.1: 77 percent / Pd(OAc)2; Ph₃P; aq. NaHCO₃ / dioxane / 12 h / Heating

3.1: toluene / 2 h / Heating

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

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

4.3: 1.70 g / hydrogen peroxide; AcOH / tetrahydrofuran; hexane / 16 h / 20 °C

5.1: 54 percent / aq. HCl / tetrahydrofuran / 0.25 h / Heating

6.1: 88 percent / K₂CO₃ / tetrahydrofuran / 3 h / Heating

7.1: 79 percent / tetrahexylammonium iodide; aq. NaOH / CH₂Cl₂

8.1: 99 percent / hydrogen / Raney nickel / methanol / 24 h

9.1: LiAlH₄ / tetrahydrofuran / 2 h / Heating

10.1: 0.50 g / Et₃N / CH₂Cl₂ / 1 h

With hydrogenchloride; palladium diacetate; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; hydrogen; sodium hydrogencarbonate; tetrahexylammonium iodide; potassium carbonate; triethylamine; triphenylphosphine; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; toluene; 2.1: Suzuki coupling;

DOI:10.1021/jo049157q

upstream raw materials:

di-tert-butyl dicarbonate

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

3,4-dihydro-2H-pyran

piperonal

Downstream raw materials:

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

(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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