(+)-(2S,3aS,8aS)-trimethyl 3a-phenyl-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate

Base Information

• Chemical Name: (+)-(2S,3aS,8aS)-trimethyl 3a-phenyl-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate
• CAS No.: 1320252-63-8
• Molecular Formula: C₂₂H₂₂N₂O₆
• Molecular Weight: 410.426

Synonyms:

Chemical Property of (+)-(2S,3aS,8aS)-trimethyl 3a-phenyl-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S,3aS,8aS)-trimethyl 3a-phenyl-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate

There total 7 articles about (+)-(2S,3aS,8aS)-trimethyl 3a-phenyl-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate 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:

(+)-(2S,3aS,8aS)-trimethyl 3a-azido-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate (1320252-13-8) → (+)-(2S,3aS,8aS)-trimethyl 3a-phenyl-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate (1320252-63-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: DL-dithiothreitol; triethylamine / methanol / 0.33 h / 23 °C / Inert atmosphere

2.1: dmap / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

2.2: 4 h / 23 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 0.17 h / 0 °C / Inert atmosphere

3.2: 3 h / 23 °C / Inert atmosphere

4.1: tert-butyl alcohol / 12 h / 23 °C / UV-irradiation; Inert atmosphere

With dmap; DL-dithiothreitol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja2057852

Reference yield:

(+)-(2S,3aS,8aS)-trimethyl 3a-bromo-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate (1320252-10-5) → (+)-(2S,3aS,8aS)-trimethyl 3a-phenyl-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate (1320252-63-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trimethylsilylazide; tin(IV) chloride / dichloromethane / 12 h / 23 °C / Inert atmosphere

2.1: DL-dithiothreitol; triethylamine / methanol / 0.33 h / 23 °C / Inert atmosphere

3.1: dmap / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

3.2: 4 h / 23 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 0.17 h / 0 °C / Inert atmosphere

4.2: 3 h / 23 °C / Inert atmosphere

5.1: tert-butyl alcohol / 12 h / 23 °C / UV-irradiation; Inert atmosphere

With dmap; DL-dithiothreitol; trimethylsilylazide; tin(IV) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja2057852

Reference yield:

(+)-(2S,3aS,8aS)-trimethyl 3a-amino-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate (1320252-14-9) → (+)-(2S,3aS,8aS)-trimethyl 3a-phenyl-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate (1320252-63-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

1.2: 4 h / 23 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 0.17 h / 0 °C / Inert atmosphere

2.2: 3 h / 23 °C / Inert atmosphere

3.1: tert-butyl alcohol / 12 h / 23 °C / UV-irradiation; Inert atmosphere

With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja2057852

upstream raw materials:

(+)-(2S,3aS,8aS)-trimethyl 3a-azido-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate

(+)-(2S,3aS,8aS)-trimethyl 3a-amino-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate

C₂₂H₂₄N₄O₈S

C₂₂H₂₂N₄O₆

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