(2R,6R,12bS,E)-benzyl 3-ethylidene-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate

Base Information

• Chemical Name: (2R,6R,12bS,E)-benzyl 3-ethylidene-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate
• CAS No.: 951327-91-6
• Molecular Formula: C₂₉H₃₂N₂O₅
• Molecular Weight: 488.583
• Mol file: 951327-91-6.mol

Synonyms:(2R,6R,12bS,E)-benzyl 3-ethylidene-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate

Chemical Property of (2R,6R,12bS,E)-benzyl 3-ethylidene-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R,12bS,E)-benzyl 3-ethylidene-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate

There total 10 articles about (2R,6R,12bS,E)-benzyl 3-ethylidene-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate 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: 75.0%

(1S,3R)-benzyl 2-((Z)-2-iodobut-2-enyl)-5-methoxy-1-((E)-4-methoxy-4-oxobut-2-enyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate (951327-86-9) → (2R,6R,12bS,E)-benzyl 3-ethylidene-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate (951327-91-6)

Guidance literature:

bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1021/ol071220l

Reference yield:

N-tert-butoxycarbonyl-2-iodo-3-methoxyaniline (194869-14-2) → (2R,6R,12bS,E)-benzyl 3-ethylidene-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate (951327-91-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 82 percent / K₂CO₃; LiCl / Pd(OAc)2 / dimethylformamide / 72 h / 100 °C

2.1: 91 percent / aq. HCl / tetrahydrofuran

3.1: NaOH / ethanol

3.2: triphosgene / tetrahydrofuran / 45 °C

3.3: 84 percent / HCl / diethyl ether / 24 h

4.1: 85 percent / Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 20 °C

5.1: CH₃COOH / CH₂Cl₂ / 24 h

5.2: 90 percent / TFA / CH₂Cl₂ / 0.5 h

6.1: PhSH; NaH / 1,2-dimethoxy-ethane / 8 h / 20 °C

6.2: m-CPBA / CH₂Cl₂ / -78 °C

6.3: 64 percent / Na₂CO₃ / toluene / Heating

7.1: 75 percent / Ni(COD)2 / acetonitrile / 0.5 h / 20 °C

With hydrogenchloride; sodium hydroxide; sodium hydride; potassium carbonate; caesium carbonate; acetic acid; thiophenol; lithium chloride; palladium diacetate; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Larock heteroannulation / 5.1: Pictet-Spengler reaction;

DOI:10.1021/ol071220l

Reference yield:

(2S)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazole (355839-96-2) → (2R,6R,12bS,E)-benzyl 3-ethylidene-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate (951327-91-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 82 percent / K₂CO₃; LiCl / Pd(OAc)2 / dimethylformamide / 72 h / 100 °C

2.1: 91 percent / aq. HCl / tetrahydrofuran

3.1: NaOH / ethanol

3.2: triphosgene / tetrahydrofuran / 45 °C

3.3: 84 percent / HCl / diethyl ether / 24 h

4.1: 85 percent / Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 20 °C

5.1: CH₃COOH / CH₂Cl₂ / 24 h

5.2: 90 percent / TFA / CH₂Cl₂ / 0.5 h

6.1: PhSH; NaH / 1,2-dimethoxy-ethane / 8 h / 20 °C

6.2: m-CPBA / CH₂Cl₂ / -78 °C

6.3: 64 percent / Na₂CO₃ / toluene / Heating

7.1: 75 percent / Ni(COD)2 / acetonitrile / 0.5 h / 20 °C

With hydrogenchloride; sodium hydroxide; sodium hydride; potassium carbonate; caesium carbonate; acetic acid; thiophenol; lithium chloride; palladium diacetate; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Larock heteroannulation / 5.1: Pictet-Spengler reaction;

DOI:10.1021/ol071220l

upstream raw materials:

(1S,3R)-benzyl 2-((Z)-2-iodobut-2-enyl)-5-methoxy-1-((E)-4-methoxy-4-oxobut-2-enyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

4-methoxy-D-tryptophan benzyl ester

(R,Z)-benzyl 2-(2-iodobut-2-enylamino)-3-(4-methoxy-1H-indol-3-yl)propanoate

(1S,3R,Z)-benzyl 2-(2-iodobut-2-enyl)-5-methoxy-1-(4-methoxy-4-oxo-3,3-bis(phenylthio)butyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

Downstream raw materials:

mitragynine