methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Base Information

• Chemical Name: methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate
• CAS No.: 219589-99-8
• Molecular Formula: C₂₈H₃₁N₃O₃
• Molecular Weight: 457.572
• Mol file: 219589-99-8.mol

Synonyms:methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Chemical Property of methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

There total 5 articles about methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 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: 75.0%

methyl (2S,3aS,5R,11bR)-2-(methoxycarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (219589-97-6) → methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (219589-99-8)

Guidance literature:

With ammonia; In methanol; for 120h; Ambient temperature;

DOI:10.1021/jo981401o

Reference yield:

methyl (2S,3aS,5R,11bR)-2-(benzyloxycarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (219589-98-7) → methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (219589-99-8)

Guidance literature:

With ammonia; In methanol; at 110 ℃; for 17h;

DOI:10.1021/jo981401o

Reference yield:

ethyl 4-methylene-(2E)-hexenoate (13369-25-0) → methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (219589-99-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

2: 80 percent / PCC / CH₂Cl₂ / 0 - 20 °C

3: 70 percent / PhCO₂H, hydroquinone / benzene / 18 h / Heating

4: NH₃ / methanol / 17 h / 110 °C

With lithium aluminium tetrahydride; ammonia; hydroquinone; benzoic acid; pyridinium chlorochromate; In methanol; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo981401o

upstream raw materials:

methyl (2S,3aS,5R,11bR)-2-(methoxycarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

methyl (2S,3aS,5R,11bR)-2-(benzyloxycarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

ethyl 4-methylene-(2E)-hexenoate

(E)-4-methylenehex-2-enal

Downstream raw materials:

methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

methyl (2S,3aS,5R,11bR)-3-(tert-butoxycarbonyl)-2,3,3a,4,5,7-hexahydro-5-(2-(1-(tosyloxy-2-hydroxy)butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

(2S,3aS,5S,11bR)-3-Benzyl-2-cyano-5-(1-methylene-propyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester