5-amino-6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-1H-indole-3-methanol acetate

Base Information

• Chemical Name: 5-amino-6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-1H-indole-3-methanol acetate
• CAS No.: 108833-10-9
• Molecular Formula: C₁₉H₂₂N₂O₅S
• Molecular Weight: 390.46
• Mol file: 108833-10-9.mol

Synonyms:5-amino-6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-1H-indole-3-methanol acetate

Chemical Property of 5-amino-6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-1H-indole-3-methanol acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-amino-6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-1H-indole-3-methanol acetate

There total 11 articles about 5-amino-6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-1H-indole-3-methanol acetate 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: 81.0%

6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-5-nitro-1H-indole-3-methanol acetate (112089-52-8) → 5-amino-6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-1H-indole-3-methanol acetate (108833-10-9)

Guidance literature:

With hydrogen; platinum(IV) oxide; In tetrahydrofuran; ethanol; for 2h; under 2068.6 Torr;

DOI:10.1021/jm00398a017

Reference yield:

6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-1H-indole-3-methanol acetate (112089-54-0) → 5-amino-6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-1H-indole-3-methanol acetate (108833-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C

2: 81 percent / hydrogen / 84.5percent PtO₂ / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr

With hydrogen; nitric acid; platinum(IV) oxide; In tetrahydrofuran; nitromethane; ethanol;

DOI:10.1021/jm00398a017

Reference yield:

6-(benzyloxy)-1-(methylsulfonyl)-3-<<(methylsulfonyl)oxy>methyl>indoline (106014-85-1) → 5-amino-6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-1H-indole-3-methanol acetate (108833-10-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride

2: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C

3: 81 percent / hydrogen / 84.5percent PtO₂ / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr

With hydrogen; nitric acid; sodium acetate; triethylamine; platinum(IV) oxide; In tetrahydrofuran; nitromethane; ethanol;

DOI:10.1021/jm00398a017

upstream raw materials:

6-(benzyloxy)-2,3-dihydro-1-(methylsulfonyl)-5-nitro-1H-indole-3-methanol acetate

3-nitro-4-chlorophenol

2-[4-(benzyloxy)-2-nitrophenyl]propane-1,3-diol

4-benzyloxy-2-nitro-chlorobenzene

Downstream raw materials:

5-(benzyloxy)-1,2,3,6,7,8-hexahydro-3-(methylsulfonyl)-8-(methylthio)-7-oxobenzo[1,2-b:4,3-b']dipyrrole-1-methanol acetate

2-acetyl-1,2,8,8a-tetrahydro-7-methylcyclopropa[c]pyrrolo[3,2-e]indol-4(5H)-one

5-(benzyloxy)-1,2,3,6-tetrahydro-8-methyl-3-(methylsulfonyl)benzo<1,2-b:4,3-b'>dipyrrole-1-methanol

5-(benzyloxy)-1,2,3,6,7,8-hexahydro-8-methyl-3-(methylsulfonyl)-8-(methylthio)-7-oxobenzo<1,2-b:4,3-b'>dipyrrole-1-methanol acetate

Refernces

• 1、 Warpehoski, M.A.. "Total Synthesis of U-71,184, A Potent New Antitumor Agent Modeled on CC-1065". . p. 4103 - 4106. Retrieved 2007/10/02.