(R)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic acid tert-butyl ester

Base Information

• Chemical Name: (R)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic acid tert-butyl ester
• CAS No.: 1266317-95-6
• Molecular Formula: C₂₅H₂₉BrN₂O₄
• Molecular Weight: 501.42
• Mol file: 1266317-95-6.mol

Synonyms:(R)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic acid tert-butyl ester

Chemical Property of (R)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic acid tert-butyl ester

There total 7 articles about (R)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic 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:

6-bromo-1H-indole (52415-29-9) + C17H23NO4 → (S)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic acid tert-butyl ester (1266318-13-1) + (R)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic acid tert-butyl ester (1266317-95-6)

Guidance literature:

With (2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one; trifluoroacetic acid; In dichloromethane; isopropyl alcohol; at -70 ℃; for 48h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol102795g

Reference yield:

N-allyl-4-methoxybenzylamine (86926-56-9) → (S)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic acid tert-butyl ester (1266318-13-1) + (R)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic acid tert-butyl ester (1266317-95-6)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran / 20 °C / Inert atmosphere

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere

3: diisobutylaluminium hydride / hexane; toluene / 0.5 h / -78 °C / Inert atmosphere

4: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 °C

5: trifluoroacetic acid; (2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one / dichloromethane; isopropyl alcohol / 48 h / -70 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sulfur trioxide pyridine complex; diisobutylaluminium hydride; triethylamine; (2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; isopropyl alcohol; toluene; 4: |Parikh-Doering Oxidation;

DOI:10.1139/cjc-2012-0221

Reference yield:

N-tert-butylcarbonyl-N-allyl-N-(4-methoxybenzyl)amine → (S)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic acid tert-butyl ester (1266318-13-1) + (R)-[2-(6-bromo-1H-indol-3-yl)-4-oxobutyl](4-methoxybenzyl)carbamic acid tert-butyl ester (1266317-95-6)

Guidance literature:

Multi-step reaction with 4 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere

2: diisobutylaluminium hydride / hexane; toluene / 0.5 h / -78 °C / Inert atmosphere

3: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 °C

4: trifluoroacetic acid; (2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one / dichloromethane; isopropyl alcohol / 48 h / -70 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sulfur trioxide pyridine complex; diisobutylaluminium hydride; triethylamine; (2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one; trifluoroacetic acid; In hexane; dichloromethane; dimethyl sulfoxide; isopropyl alcohol; toluene; 3: |Parikh-Doering Oxidation;

DOI:10.1139/cjc-2012-0221

upstream raw materials:

6-bromo-1H-indole

N-allyl-4-methoxybenzylamine

N-[(4-methoxyphenyl)methylidene]-N-allylamine

4-methoxy-benzaldehyde