1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-6-benzyloxyindole

Base Information

• Chemical Name: 1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-6-benzyloxyindole
• CAS No.: 294862-88-7
• Molecular Formula: C₂₂H₂₅NO₃
• Molecular Weight: 351.445
• Mol file: 294862-88-7.mol

Synonyms:1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-6-benzyloxyindole

Chemical Property of 1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-6-benzyloxyindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-6-benzyloxyindole

There total 3 articles about 1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-6-benzyloxyindole 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: 93.3%

6-benzyloxy-1H-indole (15903-94-3) + methanesulfonic acid 2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-ethyl ester (83470-62-6) → 1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-6-benzyloxyindole (294862-88-7)

Guidance literature:

6-benzyloxy-1H-indole; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

methanesulfonic acid 2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-ethyl ester; In N,N-dimethyl-formamide; at 60 ℃; for 1.5h;

DOI:10.1021/jm0306374

Reference yield:

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol (32233-43-5) → 1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-6-benzyloxyindole (294862-88-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

2.1: NaH / dimethylformamide / 0.5 h / 20 °C

2.2: 93.3 percent / dimethylformamide / 1.5 h / 60 °C

With sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0306374

Reference yield:

methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate (95422-24-5) → 1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-6-benzyloxyindole (294862-88-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaBH₄ / methanol / 3 h / 0 - 20 °C

2.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

3.1: NaH / dimethylformamide / 0.5 h / 20 °C

3.2: 93.3 percent / dimethylformamide / 1.5 h / 60 °C

With sodium tetrahydroborate; sodium hydride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0306374

upstream raw materials:

6-benzyloxy-1H-indole

methanesulfonic acid 2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-ethyl ester

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate

Downstream raw materials:

1-[(R)-1-(tert-butyldimethylsilyloxy)-4-[6-(3-(4-chlorophenyl)propoxy)indol-1-yl]-2-butyl]imidazole-4-carboxamide

1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(4-phenylbutoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide

1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-phenylpropoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide

1-[(R)-4-(6-benzyloxyindol-1-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide

Refernces