(R)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Base Information

• Chemical Name: (R)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS No.: 1395097-93-4
• Molecular Formula: C₂₉H₃₆N₂O
• Molecular Weight: 428.618

Synonyms:(R)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Chemical Property of (R)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

There total 4 articles about (R)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 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: 56.0%

C26H32N2O + allyl bromide (106-95-6) → (S)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1395097-96-7) + (R)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1395097-93-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 1h; diastereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0031-1291143

Reference yield:

(S,E)-4-((methoxymethoxy)methyl)hex-3-en-2-ol (1395097-86-5) → (S)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1395097-96-7) + (R)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1395097-93-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: propionic acid / toluene / 15 h / 120 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / ethanol / 12 h / Reflux; Inert atmosphere

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

6.1: trifluoroacetic acid / dichloromethane / 8 h / -78 - -20 °C / Inert atmosphere

7.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / Inert atmosphere

With lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; propionic acid; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 1.1: Johnson-Claisen rearrangement / 6.1: Pictet-Spengler cyclisation;

DOI:10.1055/s-0031-1291143

Reference yield:

(S,E)-ethyl 3-ethyl-3-((methoxymethoxy)methyl)hex-4-enoate (1395097-87-6) → (S)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1395097-96-7) + (R)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1395097-93-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / ethanol / 12 h / Reflux; Inert atmosphere

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 8 h / -78 - -20 °C / Inert atmosphere

6.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / Inert atmosphere

With lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; mineral oil; 5.1: Pictet-Spengler cyclisation;

DOI:10.1055/s-0031-1291143

upstream raw materials:

(S,E)-4-((methoxymethoxy)methyl)hex-3-en-2-ol

(S,E)-ethyl 3-ethyl-3-((methoxymethoxy)methyl)hex-4-enoate

(S,E)-(((3-ethyl-3-((methoxymethoxy)methyl)hex-4-en-1-yl)oxy)methyl)benzene

allyl bromide

Downstream raw materials:

(1S,12bR)-1-(2-(benzyloxy)ethyl)-1-ethyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine

(-)-eburnamonine

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