[(2S,6R,12bR)-12-Benzyl-13-methylene-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-acetic acid methyl ester

Base Information

• Chemical Name: [(2S,6R,12bR)-12-Benzyl-13-methylene-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-acetic acid methyl ester
• CAS No.: 119184-30-4
• Molecular Formula: C₂₇H₂₆N₂O₂
• Molecular Weight: 410.516
• Mol file: 119184-30-4.mol

Synonyms:[(2S,6R,12bR)-12-Benzyl-13-methylene-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-acetic acid methyl ester

Chemical Property of [(2S,6R,12bR)-12-Benzyl-13-methylene-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,6R,12bR)-12-Benzyl-13-methylene-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-acetic acid methyl ester

There total 22 articles about [(2S,6R,12bR)-12-Benzyl-13-methylene-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-acetic acid methyl 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: 13.0%

[(2S,6R,12bR)-12-Benzyl-13-oxo-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-acetic acid methyl ester (119184-29-1,119241-72-4) + 1,1-dibromomethane (74-95-3) → [(2S,6R,12bR)-12-Benzyl-13-methylene-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-acetic acid methyl ester (119184-30-4) + C28H28N2O2 (119184-31-5)

Guidance literature:

With titanium tetrachloride; zinc; at 15 ℃;

DOI:10.1021/ja00184a086

Reference yield:

(S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester (129708-73-2) → (E)-(2S,6R,12bR)-(+)-methyl 12-benzyl-13-methylene-1,2,3,4,5,6,7,12,12b-octahydro-2,6-methanoindolo<2,3-a>quinolizine-3-ethylidenoate (119184-30-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 95 percent / sodium borohydride / methanol / 1 h / 25 °C

2: 67 percent / benzene; dioxane / 24 h / Heating

3: chlorotrimethylsilane / 25 °C

4: 72 percent / NaH, MeOH / toluene / 16 h / Heating

5: 99 percent / HOAc, H₂SO₄ / H₂O / 72 h / Heating

6: 85 percent / 88percent aq. formic acid / 10percent Pd/C / 2 h / Ambient temperature

7: 60 percent / K₂CO₃ / ethanol; toluene / 12 h / Ambient temperature

8: 82 percent / Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

9: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) from -78 deg C to -30 deg C

10: 91 percent / lithium tetrafluoroborate / tetrahydrofuran; acetonitrile / 72 h / Heating

11: 71 percent / pyrrolidine, trifluoroacetic acid / benzene / 19 h / Heating

12: 1.) titanocene dichloride / 1.) toluene, RT, 3 d, 2.) THF, RT, 40 min

With pyrrolidine; methanol; sodium tetrahydroborate; lithium tetrafluoroborate; n-butyllithium; chloro-trimethyl-silane; formic acid; titanocene dichloride; sulfuric acid; sodium hydride; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; toluene; acetonitrile; benzene;

DOI:10.1021/ja00169a033

Reference yield:

(6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (129708-76-5) → (E)-(2S,6R,12bR)-(+)-methyl 12-benzyl-13-methylene-1,2,3,4,5,6,7,12,12b-octahydro-2,6-methanoindolo<2,3-a>quinolizine-3-ethylidenoate (119184-30-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / 88percent aq. formic acid / 10percent Pd/C / 2 h / Ambient temperature

2: 60 percent / K₂CO₃ / ethanol; toluene / 12 h / Ambient temperature

3: 82 percent / Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) from -78 deg C to -30 deg C

5: 91 percent / lithium tetrafluoroborate / tetrahydrofuran; acetonitrile / 72 h / Heating

6: 71 percent / pyrrolidine, trifluoroacetic acid / benzene / 19 h / Heating

7: 1.) titanocene dichloride / 1.) toluene, RT, 3 d, 2.) THF, RT, 40 min

With pyrrolidine; lithium tetrafluoroborate; n-butyllithium; formic acid; titanocene dichloride; potassium carbonate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1021/ja00169a033

upstream raw materials:

trimethylaluminum

(E)-(2S,6R,12bR)-(+)-methyl 12-benzyl-13-oxo-1,2,3,4,5,6,7,12,12b-octahydro-2,6-methanoindolo<2,3-a>quinolizine-3-ethylidenoate

1,1-dibromomethane

(6R,10R)-(+)-5-benzyl-9-oxo-12-(prop-2-ynyl)-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Downstream raw materials:

E-koumidine

(+)-taberpsychine

2-[(2R,6R,12bR)-12-Benzyl-13-hydroxymethyl-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-ethanol

[(2R,6R,12bR)-12-Benzyl-13-hydroxymethyl-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-acetic acid methyl ester