5-Benzyloxy-3-(tert-butyloxycarbonyl)-8-cyano-1-[(2',2',6',6'-tetramethylpiperidino)oxy]methyl-1,2-dihydro-3H-benz[e]indole

Base Information

• Chemical Name: 5-Benzyloxy-3-(tert-butyloxycarbonyl)-8-cyano-1-[(2',2',6',6'-tetramethylpiperidino)oxy]methyl-1,2-dihydro-3H-benz[e]indole
• CAS No.: 178877-19-5
• Molecular Formula: C₃₅H₄₃N₃O₄
• Molecular Weight: 569.744
• Mol file: 178877-19-5.mol

Synonyms:5-Benzyloxy-3-(tert-butyloxycarbonyl)-8-cyano-1-[(2',2',6',6'-tetramethylpiperidino)oxy]methyl-1,2-dihydro-3H-benz[e]indole

Chemical Property of 5-Benzyloxy-3-(tert-butyloxycarbonyl)-8-cyano-1-[(2',2',6',6'-tetramethylpiperidino)oxy]methyl-1,2-dihydro-3H-benz[e]indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Benzyloxy-3-(tert-butyloxycarbonyl)-8-cyano-1-[(2',2',6',6'-tetramethylpiperidino)oxy]methyl-1,2-dihydro-3H-benz[e]indole

There total 9 articles about 5-Benzyloxy-3-(tert-butyloxycarbonyl)-8-cyano-1-[(2',2',6',6'-tetramethylpiperidino)oxy]methyl-1,2-dihydro-3H-benz[e]indole 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: 68.0%

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) + N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine (178877-18-4) → 5-Benzyloxy-3-(tert-butyloxycarbonyl)-8-cyano-1-[(2',2',6',6'-tetramethylpiperidino)oxy]methyl-1,2-dihydro-3H-benz[e]indole (178877-19-5)

Guidance literature:

With tri-n-butyl-tin hydride; In benzene; at 60 ℃; for 2.41667h;

DOI:10.1021/jo9605298

Reference yield:

Bu3 SnH + ethyl acetate n-hexane + N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine (178877-18-4) → 5-Benzyloxy-3-(tert-butyloxycarbonyl)-8-cyano-1-[(2',2',6',6'-tetramethylpiperidino)oxy]methyl-1,2-dihydro-3H-benz[e]indole (178877-19-5)

Guidance literature:

With cyfluthrin; SiO₂; In benzene;

Reference yield:

7-Bromo-4-hydroxynaphthalene-2-carboxylic acid ethyl ester (178876-99-8) → 5-Benzyloxy-3-(tert-butyloxycarbonyl)-8-cyano-1-[(2',2',6',6'-tetramethylpiperidino)oxy]methyl-1,2-dihydro-3H-benz[e]indole (178877-19-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / K₂CO₃, Bu₄NI / dimethylformamide / 11 h / 25 °C

2: 96 percent / dimethylformamide / 20 h / Heating

3: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 25 h / 25 °C

4: 87 percent / Et₃N, diphenyl phosphorazidate / 14 h / Heating

5: 68 percent / NIS, TsOH*H₂O / tetrahydrofuran; methanol / 1) -40 deg C, 1 h, 2) 25 deg C, 1 h

6: 1) NaH / 1) DMF, 0 deg C, 30 min, 2) DMF, 25 deg C, 2 h

7: 68 percent / Bu₃SnH / benzene / 2.42 h / 60 °C

With lithium hydroxide; N-iodo-succinimide; diphenyl phosphoryl azide; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo9605298

upstream raw materials:

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine

7-Bromo-4-hydroxynaphthalene-2-carboxylic acid ethyl ester

4-Acetoxy-7-bromo-naphthalene-2-carboxylic acid ethyl ester

Downstream raw materials:

(+)-(1R)-5-benzyloxy-3-tert-butoxycarbonyl-1-chloromethyl-8-cyano-1,2-dihydro-3H-benz[e]indole

(-)-(1S)-5-benzyloxy-3-tert-butoxycarbonyl-1-chloromethyl-8-cyano-1,2-dihydro-3H-benz[e]indole

rac-5-benzyloxy-3-tert-butoxycarbonyl-1-chloromethyl-8-cyano-1,2-dihydro-3H-benz[e]indole

5-Benzyloxy-8-cyano-1-hydroxymethyl-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester