benzyl (2S,3aR,4S,7aS)-4-[(tert-butoxycarbonyl)amino]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate

Base Information

• Chemical Name: benzyl (2S,3aR,4S,7aS)-4-[(tert-butoxycarbonyl)amino]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate
• CAS No.: 1358576-58-5
• Molecular Formula: C₂₅H₃₀N₂O₅
• Molecular Weight: 438.524
• Mol file: 1358576-58-5.mol

Synonyms:benzyl (2S,3aR,4S,7aS)-4-[(tert-butoxycarbonyl)amino]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate

Chemical Property of benzyl (2S,3aR,4S,7aS)-4-[(tert-butoxycarbonyl)amino]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,3aR,4S,7aS)-4-[(tert-butoxycarbonyl)amino]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate

There total 2 articles about benzyl (2S,3aR,4S,7aS)-4-[(tert-butoxycarbonyl)amino]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-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: 78.0%

(2S,3aR,4S,7aS)-1-[(benzyloxy)carbonyl]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-4-carboxylic acid (1358576-51-8) + tert-butyl alcohol (75-65-0) → benzyl (2S,3aR,4S,7aS)-4-[(tert-butoxycarbonyl)amino]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate (1358576-58-5)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; for 4h; Reflux;

DOI:10.1002/ejoc.201100996

Reference yield:

1-benzyl 4-ethyl 2-(furan-2-yl)-3,3a,4,5-tetrahydro-1H-indole-1,4(2H,7aH)-dicarboxylate → benzyl (2S,3aR,4S,7aS)-4-[(tert-butoxycarbonyl)amino]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate (1358576-58-5)

Guidance literature:

Multi-step reaction with 2 steps

1: water; lithium hydroxide / tetrahydrofuran / 19 h / 20 °C

2: diphenyl phosphoryl azide; triethylamine / 4 h / Reflux

With diphenyl phosphoryl azide; water; triethylamine; lithium hydroxide; In tetrahydrofuran; 2: Curtius rearrangement;

DOI:10.1002/ejoc.201100996

Reference yield: 98.0%

benzyl (2S,3aR,4S,7aS)-4-[(tert-butoxycarbonyl)amino]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate (1358576-58-5) → benzyl (2S,3aR,4S,7aS)-4-amino-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate (1358576-53-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; at 20 ℃; for 0.75h;

DOI:10.1002/ejoc.201100996

upstream raw materials:

(2S,3aR,4S,7aS)-1-[(benzyloxy)carbonyl]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-4-carboxylic acid

tert-butyl alcohol

Downstream raw materials:

benzyl (2S,3aR,4S,7aS)-4-amino-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate