(6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

Base Information

• Chemical Name: (6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde
• CAS No.: 219583-98-9
• Molecular Formula: C₂₈H₃₂N₂O
• Molecular Weight: 412.575
• Mol file: 219583-98-9.mol

Synonyms:(6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

Chemical Property of (6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

There total 4 articles about (6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde 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: 95.0%

(6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde (217448-26-5) + methyl iodide (74-88-4) → (6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde (219583-98-9)

Guidance literature:

With potassium hydride; In tetrahydrofuran; for 6h; Ambient temperature;

DOI:10.1021/jo981815h

Reference yield:

(6S,10S)-5-methyl-9-(1'-hydroxy-hex-3'-enyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole → (6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde (219583-98-9) + (6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde + (6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

Guidance literature:

With 18-crown-6 ether; potassium hydride; In 1,4-dioxane; for 2h; Yield given; Yields of byproduct given; Heating;

DOI:10.1021/ja990184l

Reference yield:

(E)-1-bromo-2-pentene (7348-71-2) → (6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde (219583-98-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / Li; biphenyl; BaI₂ / tetrahydrofuran / -78 °C

2.1: KH; 18-crown-6 / dioxane / 14 h / 100 °C

2.2: 85 percent / methanol / 6 h / 20 °C

3.1: 95 percent / NaH / tetrahydrofuran / 8 h / 0 - 20 °C

With 18-crown-6 ether; biphenyl; barium(II) iodide; lithium; potassium hydride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; 1.1: Addition / 2.1: Rearrangement / 2.2: epimerization / 3.1: Methylation;

DOI:10.1021/jo000126e

upstream raw materials:

(6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

methyl iodide

(E)-1-bromo-2-pentene

(6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole

Downstream raw materials:

(6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane

C₂₇H₃₀N₂O

alstonisine

C₂₈H₃₂N₂O₂