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

Base Information

• Chemical Name: 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
• CAS No.: 119184-33-7
• Molecular Formula: C₂₆H₂₈N₂O₂
• Molecular Weight: 400.521

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 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

There total 38 articles about 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 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: 91.9%

(Z)-(+)-(16S)-12-benzyl-10-desoxy-18-oxo-18-methoxysarpagine (119184-32-6,129784-67-4) → (Z)-(+)-(16S)-12-benzyl-10-desoxy-18-hydroxysarpagine (119184-33-7,129784-68-5)

Guidance literature:

With diisobutylaluminium hydride; In toluene; benzene; for 1h; Ambient temperature;

DOI:10.1021/ja00169a033

Reference yield: 85.0%

(E)-(+)-(16S)-12-benzyl-10-desoxy-18-oxo-18-methoxysarpagine (119184-32-6,129784-67-4) → (E)-(+)-(16S)-12-benzyl-10-desoxy-18-hydroxysarpagine (119184-33-7,129784-68-5)

Guidance literature:

With diisobutylaluminium hydride; In toluene; benzene; for 1h; Ambient temperature;

DOI:10.1021/ja00169a033

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)-(+)-(16S)-12-benzyl-10-desoxy-18-hydroxysarpagine (119184-33-7,129784-68-5)

Guidance literature:

Multi-step reaction with 14 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

13: 1.) diisoamylborane, 2.) 10percent aq. NaOH, 30percent H₂O₂ / 1.) DMF, RT, 4 h, 2.) RT, 1 h

14: 85 percent / diisobutylaluminum hydride / benzene; toluene / 1 h / Ambient temperature

With pyrrolidine; methanol; sodium hydroxide; sodium tetrahydroborate; lithium tetrafluoroborate; n-butyllithium; chloro-trimethyl-silane; formic acid; diisoamyl borane; titanocene dichloride; sulfuric acid; dihydrogen peroxide; sodium hydride; diisobutylaluminium 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

upstream raw materials:

(Z)-(+)-(16S)-12-benzyl-10-desoxy-18-oxo-18-methoxysarpagine

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

(S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester

(6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Downstream raw materials:

(+)-koumidine

(+)-koumine

(E)-(+)-(16S)-10-desoxysarpagine

(E)-(+)-(16S)-10-desoxy-18-hydroxysarpagine

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