(3aR,4S,11bS)-3-Benzyl-4-((S)-2-methoxycarbonyl-butyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester

Base Information

• Chemical Name: (3aR,4S,11bS)-3-Benzyl-4-((S)-2-methoxycarbonyl-butyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester
• CAS No.: 109704-78-1
• Molecular Formula: C₂₉H₃₄N₂O₄
• Molecular Weight: 474.6
• Mol file: 109704-78-1.mol

Synonyms:

Chemical Property of (3aR,4S,11bS)-3-Benzyl-4-((S)-2-methoxycarbonyl-butyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,11bS)-3-Benzyl-4-((S)-2-methoxycarbonyl-butyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester

There total 5 articles about (3aR,4S,11bS)-3-Benzyl-4-((S)-2-methoxycarbonyl-butyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic 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: 32.0%

methyl 2-ethyl-5-oxopentanoate (109704-76-9) + 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester (146681-75-6) → 2,16-Didehydro-16,20-bis(methoxycarbonyl)-21-phenyl-20,21-seco-pseudoaspidospermidine (3α,14β,20αβ) (109704-78-1,121153-56-8,121155-14-4)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 48h; Heating;

DOI:10.1021/jo00074a039

Reference yield:

3-ethyl-tetrahydro-pyran-2-one (32821-68-4,103957-83-1) → (3aR,4S,11bS)-3-Benzyl-4-((S)-2-methoxycarbonyl-butyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester (109704-78-1,121153-56-8,121155-14-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / H₂SO₄ conc. / 17 h / 20 °C

2: 59 percent / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h / 20 °C

3: 82 percent / methanol / 12 h / 20 °C

4: 2.) triethylamine / 1.) ether, 20 deg C, 48 h 2.) methanol, reflux, 5 h

With sulfuric acid; triethylamine; pyridinium chlorochromate; In methanol; dichloromethane;

DOI:10.1021/jo00275a029

Reference yield:

methyl 2-ethyl-5-oxopentanoate (109704-76-9) → (3aR,4S,11bS)-3-Benzyl-4-((S)-2-methoxycarbonyl-butyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester (109704-78-1,121153-56-8,121155-14-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / methanol / 12 h / 20 °C

2: 2.) triethylamine / 1.) ether, 20 deg C, 48 h 2.) methanol, reflux, 5 h

With triethylamine; In methanol;

DOI:10.1021/jo00275a029

upstream raw materials:

methyl 2-ethyl-5-oxopentanoate

2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester

benzyl bromide

C₂₂H₂₈N₂O₄

Downstream raw materials:

(+/-)-14-Epipseudovincadifformine