1-[4-(t-butyldimethylsilyloxy)phenyl]-1-hydroxy-3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Base Information

• Chemical Name: 1-[4-(t-butyldimethylsilyloxy)phenyl]-1-hydroxy-3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• CAS No.: 919519-17-8
• Molecular Formula: C₂₉H₃₇NO₂Si
• Molecular Weight: 459.704
• Mol file: 919519-17-8.mol

Synonyms:1-[4-(t-butyldimethylsilyloxy)phenyl]-1-hydroxy-3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Chemical Property of 1-[4-(t-butyldimethylsilyloxy)phenyl]-1-hydroxy-3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[4-(t-butyldimethylsilyloxy)phenyl]-1-hydroxy-3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

There total 5 articles about 1-[4-(t-butyldimethylsilyloxy)phenyl]-1-hydroxy-3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 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: 50.0%

4-t-butyldimethylsilyloxy-N-[2-(2-iodophenyl)ethyl]-N-methyl-α-phenylphenacylamine (919519-07-6) → 1-[4-(t-butyldimethylsilyloxy)phenyl]-1-hydroxy-3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (919519-17-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 0.5h;

DOI:10.3987/com-06-10853

Reference yield:

1-(4-((tert-butyldimethylsilyl)oxy)phenyl)-2-phenylethan-1-one (163083-22-5) → 1-[4-(t-butyldimethylsilyloxy)phenyl]-1-hydroxy-3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (919519-17-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 43.3 percent / benzyltrimethyl-ammonium tribromide / CH₂Cl₂; methanol / 5 h / Heating

2: 83.3 percent / propylene oxide / dioxane / 1.5 h / 110 °C

3: 50 percent / n-C₄H₉Li / hexane; tetrahydrofuran / 0.5 h / 20 °C

With n-butyllithium; benzyltrimethylammonium tribromide; methyloxirane; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; 3: intramolecular Barbier reaction;

DOI:10.3987/com-06-10853

Reference yield:

1-(4-Hydroxyphenyl)-2-phenylethanone (2491-32-9) → 1-[4-(t-butyldimethylsilyloxy)phenyl]-1-hydroxy-3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (919519-17-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 96.4 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

2: 43.3 percent / benzyltrimethyl-ammonium tribromide / CH₂Cl₂; methanol / 5 h / Heating

3: 83.3 percent / propylene oxide / dioxane / 1.5 h / 110 °C

4: 50 percent / n-C₄H₉Li / hexane; tetrahydrofuran / 0.5 h / 20 °C

With 1H-imidazole; n-butyllithium; benzyltrimethylammonium tribromide; methyloxirane; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; 4: intramolecular Barbier reaction;

DOI:10.3987/com-06-10853

upstream raw materials:

4-t-butyldimethylsilyloxy-N-[2-(2-iodophenyl)ethyl]-N-methyl-α-phenylphenacylamine

1-(4-((tert-butyldimethylsilyl)oxy)phenyl)-2-phenylethan-1-one

1-(4-Hydroxyphenyl)-2-phenylethanone

tert-butyldimethylsilyl chloride

Refernces