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

Base Information

• Chemical Name: (S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester
• CAS No.: 129708-73-2
• Molecular Formula: C₂₆H₂₄N₂O₂
• Molecular Weight: 396.489
• Mol file: 129708-73-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic 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:

N1-benzyl-(L)-tryptophan methyl ester (129784-64-1) + benzaldehyde (100-52-7) → (S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester (129708-73-2)

Guidance literature:

In benzene; for 12h;

DOI:10.1021/ja00169a033

Reference yield: 95.0%

(S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester (129708-73-2) → (S)-(-)-N,N'-dibenzyltryptophan methyl ester (119184-20-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 25 ℃; for 1h;

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) → (+)-koumine (1358-76-5,83705-29-7,119241-69-9)

Guidance literature:

Multi-step reaction with 17 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: 14 percent / pyrrolidine, trifluoroacetic acid / benzene / 19 h / Heating

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

13: 91.9 percent / diisobutylaluminum hydride / benzene; toluene / 1 h / Ambient temperature

14: 91 percent / Na, NH₃ (liquid) / tetrahydrofuran / 1.5 h / -78 °C

15: 43 percent / tetrahydrofuran / 16 h / Ambient temperature

16: 76 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating

17: 40 percent / diethyl azodicarboxylate, triphenylphosphine, imidazole, sodium hydride / tetrahydrofuran / 3 h / Heating

With pyrrolidine; 1H-imidazole; methanol; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; lithium tetrafluoroborate; n-butyllithium; chloro-trimethyl-silane; formic acid; diisoamyl borane; sulfuric acid; ammonia; dihydrogen peroxide; sodium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; toluene; acetonitrile; benzene;

DOI:10.1021/ja00169a033

upstream raw materials:

N¹-benzyl-(L)-tryptophan methyl ester

benzaldehyde

Downstream raw materials:

(S)-(-)-N,N'-dibenzyltryptophan methyl ester

(+)-taberpsychine

(+)-koumine

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

Refernces