benzyl (2S,3aR,4S,7aS)-4-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-amino-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate
CAS No.:1358576-53-0
Molecular Formula:C₂₀H₂₂N₂O₃
Molecular Weight:338.406
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 3 articles about benzyl (2S,3aR,4S,7aS)-4-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: 98.0%

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

: 1358576-53-0
benzyl (2S,3aR,4S,7aS)-4-amino-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate

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

: 1358576-53-0
benzyl (2S,3aR,4S,7aS)-4-amino-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: trifluoroacetic acid / dichloromethane; water / 0.75 h / 20 °C

With diphenyl phosphoryl azide; water; triethylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; 2: Curtius rearrangement;
DOI:10.1002/ejoc.201100996

Reference yield:

: 1358576-51-8
(2S,3aR,4S,7aS)-1-[(benzyloxy)carbonyl]-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-4-carboxylic acid

: 1358576-53-0
benzyl (2S,3aR,4S,7aS)-4-amino-2-(furan-2-yl)-2,3,3a,4,5,7a-hexahydro-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

2: trifluoroacetic acid / dichloromethane; water / 0.75 h / 20 °C

With diphenyl phosphoryl azide; triethylamine; trifluoroacetic acid; In dichloromethane; water; 1: Curtius rearrangement;
DOI:10.1002/ejoc.201100996