(1R,12bS)-1-ethyl-2,3,6,7,12,12b-hexahydro-1-[2-(phenylseleno)ethyl]indolo[2,3-a]quinolizin-4(1H)-one

Base Information

• Chemical Name: (1R,12bS)-1-ethyl-2,3,6,7,12,12b-hexahydro-1-[2-(phenylseleno)ethyl]indolo[2,3-a]quinolizin-4(1H)-one
• CAS No.: 442632-38-4
• Molecular Formula: C₂₅H₂₈N₂OSe
• Molecular Weight: 451.47
• Mol file: 442632-38-4.mol

Synonyms:(1R,12bS)-1-ethyl-2,3,6,7,12,12b-hexahydro-1-[2-(phenylseleno)ethyl]indolo[2,3-a]quinolizin-4(1H)-one

Chemical Property of (1R,12bS)-1-ethyl-2,3,6,7,12,12b-hexahydro-1-[2-(phenylseleno)ethyl]indolo[2,3-a]quinolizin-4(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,12bS)-1-ethyl-2,3,6,7,12,12b-hexahydro-1-[2-(phenylseleno)ethyl]indolo[2,3-a]quinolizin-4(1H)-one

There total 6 articles about (1R,12bS)-1-ethyl-2,3,6,7,12,12b-hexahydro-1-[2-(phenylseleno)ethyl]indolo[2,3-a]quinolizin-4(1H)-one 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: 88.0%

diphenyl diselenide (1666-13-3) + (1R,12bS)-1-ethyl-2,3,6,7,12,12b-hexahydro-1-[2-[(methanesulfonyl)oxy]ethyl]indolo[2,3-a]quinolizin-4(1H)-one (442632-36-2) → (3R,16S)-14,15-dihydroeburnamenin-19-one (690993-38-5) + (1R,12bS)-1-ethyl-2,3,6,7,12,12b-hexahydro-1-[2-(phenylseleno)ethyl]indolo[2,3-a]quinolizin-4(1H)-one (442632-38-4)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.tet.2004.02.015

Reference yield:

3-((R)-3-Ethyl-2-methoxy-tetrahydro-furan-3-yl)-propionic acid (442632-33-9,690993-27-2) → (1R,12bS)-1-ethyl-2,3,6,7,12,12b-hexahydro-1-[2-(phenylseleno)ethyl]indolo[2,3-a]quinolizin-4(1H)-one (442632-38-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 44 percent / 144 h / 125 °C

2: 85 percent / aq. NaOH / methanol / 1 h / 20 °C

3: 90 percent / 4-(dimethylamino)pyridine; pyridine / 2 h / 0 °C

4: 88 percent / sodium borohydride / ethanol / 3 h / 0 - 20 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; In methanol; ethanol;

DOI:10.1016/j.tet.2004.02.015

Reference yield:

(2R)-2,3-dideoxy-2-ethyl-2-(2-propenyl)-D-glyceropentanoic acid γ-lactone (81075-90-3) → (1R,12bS)-1-ethyl-2,3,6,7,12,12b-hexahydro-1-[2-(phenylseleno)ethyl]indolo[2,3-a]quinolizin-4(1H)-one (442632-38-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: aq. NaOH / dioxane / 1 h / 100 °C

1.2: 95 percent / sodium periodate / H₂O / 3 h / 20 °C

2.1: 92 percent / sodium borohydride / methanol / 1 h / 20 °C

3.1: diisobutylaluminum hydride / diethyl ether / 1 h / -78 °C

3.2: 84 percent / p-toluenesulfonic acid / methanol / 0.67 h / Heating

4.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran; hexane / 20 °C

4.2: 87 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; hexane / 0 - 20 °C

5.1: sulfur trioxide pyridine complex; methyl sulfoxide; triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 95 percent / 2-methyl-2-butene; sodium dihydrogenphosphate dihydrate; sodium chlorite / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

7.1: 44 percent / 144 h / 125 °C

8.1: 85 percent / aq. NaOH / methanol / 1 h / 20 °C

9.1: 90 percent / 4-(dimethylamino)pyridine; pyridine / 2 h / 0 °C

10.1: 88 percent / sodium borohydride / ethanol / 3 h / 0 - 20 °C

With pyridine; dmap; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; sulfur trioxide pyridine complex; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/j.tet.2004.02.015

upstream raw materials:

diphenyl diselenide

(1R,12bS)-1-ethyl-2,3,6,7,12,12b-hexahydro-1-[2-[(methanesulfonyl)oxy]ethyl]indolo[2,3-a]quinolizin-4(1H)-one

(3R)-3-ethyldihydro-3-(2-propenyl)-2(3H)-furanone

3-((R)-3-Ethyl-2-methoxy-tetrahydro-furan-3-yl)-propionic acid