5-Benzyloxy-8-methoxy-1-(tetrahydro-pyran-2-yloxymethyl)-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 5-Benzyloxy-8-methoxy-1-(tetrahydro-pyran-2-yloxymethyl)-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester
• CAS No.: 173483-61-9
• Molecular Formula: C₃₁H₃₇NO₆
• Molecular Weight: 519.638
• Mol file: 173483-61-9.mol

Synonyms:5-Benzyloxy-8-methoxy-1-(tetrahydro-pyran-2-yloxymethyl)-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester

Chemical Property of 5-Benzyloxy-8-methoxy-1-(tetrahydro-pyran-2-yloxymethyl)-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Benzyloxy-8-methoxy-1-(tetrahydro-pyran-2-yloxymethyl)-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester

There total 9 articles about 5-Benzyloxy-8-methoxy-1-(tetrahydro-pyran-2-yloxymethyl)-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester 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: 95.0%

(4-Benzyloxy-1-bromo-7-methoxy-naphthalen-2-yl)-[(E)-3-(tetrahydro-pyran-2-yloxy)-allyl]-carbamic acid tert-butyl ester → 5-Benzyloxy-8-methoxy-1-(tetrahydro-pyran-2-yloxymethyl)-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester (173483-61-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 2h; Heating;

DOI:10.1021/jo952033g

Reference yield:

benzyl bromide (100-39-0) → 5-Benzyloxy-8-methoxy-1-(tetrahydro-pyran-2-yloxymethyl)-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester (173483-61-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / K₂CO₃, Bu₄NI / dimethylformamide / 5 h / 25 °C

2: 95 percent / LiOH, H₂O / tetrahydrofuran; methanol / 18 h / 23 °C

3: 68 percent / DPPA, Et₃N / 10 h / Heating

4: 96 percent / conc. H₂SO₄, NBS / tetrahydrofuran / 2 h / -78 °C

5: 95 percent / NaH / paraffin; dimethylformamide / 8 h / 24 °C

6: 1.) O₃, O₂, 2.) Me₂S / 1.) CH₃OH, CH₂Cl₂, -78 deg C, 2.9 min, 2.) -78 deg C, 5 min; 24 deg C, 6 h

7: 88 percent / n-BuLi, HMPA / tetrahydrofuran; hexane / 1.) -78 deg C, 5 min, 2.) -78 deg C, 20 min; 24 deg C, 5 h

8: 95 percent / AIBN, Bu₃SnH / benzene / 2 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; N-Bromosuccinimide; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); sulfuric acid; diphenyl-phosphinic acid; water; oxygen; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; ozone; triethylamine; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; paraffin; benzene;

DOI:10.1021/jo952033g

Reference yield:

ethyl 1-hydroxy-6-methoxynaphthalene-3-carboxylate (173483-53-9) → 5-Benzyloxy-8-methoxy-1-(tetrahydro-pyran-2-yloxymethyl)-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester (173483-61-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / K₂CO₃, Bu₄NI / dimethylformamide / 5 h / 25 °C

2: 95 percent / LiOH, H₂O / tetrahydrofuran; methanol / 18 h / 23 °C

3: 68 percent / DPPA, Et₃N / 10 h / Heating

4: 96 percent / conc. H₂SO₄, NBS / tetrahydrofuran / 2 h / -78 °C

5: 95 percent / NaH / paraffin; dimethylformamide / 8 h / 24 °C

6: 1.) O₃, O₂, 2.) Me₂S / 1.) CH₃OH, CH₂Cl₂, -78 deg C, 2.9 min, 2.) -78 deg C, 5 min; 24 deg C, 6 h

7: 88 percent / n-BuLi, HMPA / tetrahydrofuran; hexane / 1.) -78 deg C, 5 min, 2.) -78 deg C, 20 min; 24 deg C, 5 h

8: 95 percent / AIBN, Bu₃SnH / benzene / 2 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; N-Bromosuccinimide; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); sulfuric acid; diphenyl-phosphinic acid; water; oxygen; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; ozone; triethylamine; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; paraffin; benzene;

DOI:10.1021/jo952033g

upstream raw materials:

benzyl bromide

ethyl 1-hydroxy-6-methoxynaphthalene-3-carboxylate

1-(benzyloxy)-6-methoxynaphthalene-3-carboxylic acid

ethyl 1-(benzyloxy)-6-methoxynaphthalene-3-carboxylate

Downstream raw materials:

5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-8-methoxy-1,2-dihydro-3H-benzindole

5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-8-methoxy-1,2-dihydro-3H-benzindole