ethyl 2-((2S,3R,12bR)-3-ethyl-4-oxo-12-tosyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate

Base Information

Chemical Name:ethyl 2-((2S,3R,12bR)-3-ethyl-4-oxo-12-tosyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate
CAS No.:909121-91-1
Molecular Formula:C₂₈H₃₂N₂O₅S
Molecular Weight:508.638
Hs Code.:

Synonyms:ethyl 2-((2S,3R,12bR)-3-ethyl-4-oxo-12-tosyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate

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Chemical Property of ethyl 2-((2S,3R,12bR)-3-ethyl-4-oxo-12-tosyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate

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Technology Process of ethyl 2-((2S,3R,12bR)-3-ethyl-4-oxo-12-tosyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate

There total 4 articles about ethyl 2-((2S,3R,12bR)-3-ethyl-4-oxo-12-tosyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate 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: 63.0%

: 909121-90-0
ethyl (E)-4-((R)-2-(2-bromobutanoyl)-9-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)but-2-enoate

: 909121-91-1
ethyl 2-((2S,3R,12bR)-3-ethyl-4-oxo-12-tosyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃;
DOI:10.1021/ja0636791

Reference yield:

: 909121-97-7
(R)-1-allyl-9-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

: 909121-91-1
ethyl 2-((2S,3R,12bR)-3-ethyl-4-oxo-12-tosyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / DCC; DMAP / CH₂Cl₂ / -10 - 20 °C

2: NaIO₄; 2,6-lutidine / OsO₄ / dioxane; H₂O / 4 h / 20 °C

3: 288 mg / CH₂Cl₂ / 2 h / 20 °C

4: 63 percent / n-BuLi / tetrahydrofuran; hexane / -78 °C

With 2,6-dimethylpyridine; dmap; sodium periodate; n-butyllithium; dicyclohexyl-carbodiimide; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; 4: intramolecular Michael addition;
DOI:10.1021/ja0636791

Reference yield:

: 1-((R)-1-allyl-9-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indol-2(9H)-yl)-2-bromobutan-1-one

: 909121-91-1
ethyl 2-((2S,3R,12bR)-3-ethyl-4-oxo-12-tosyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate

Guidance literature:: Multi-step reaction with 3 steps

1: NaIO₄; 2,6-lutidine / OsO₄ / dioxane; H₂O / 4 h / 20 °C

2: 288 mg / CH₂Cl₂ / 2 h / 20 °C

3: 63 percent / n-BuLi / tetrahydrofuran; hexane / -78 °C

With 2,6-dimethylpyridine; sodium periodate; n-butyllithium; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; 3: intramolecular Michael addition;
DOI:10.1021/ja0636791