(S)-tert-butyl 4-(2-(2-(tert-butyldimethylsilyl)-1-tosyl-1H-indol-3-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 4-(2-(2-(tert-butyldimethylsilyl)-1-tosyl-1H-indol-3-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS No.: 1350542-14-1
• Molecular Formula: C₃₃H₄₈N₂O₅SSi
• Molecular Weight: 612.906
• Mol file: 1350542-14-1.mol

Synonyms:(S)-tert-butyl 4-(2-(2-(tert-butyldimethylsilyl)-1-tosyl-1H-indol-3-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property of (S)-tert-butyl 4-(2-(2-(tert-butyldimethylsilyl)-1-tosyl-1H-indol-3-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl 4-(2-(2-(tert-butyldimethylsilyl)-1-tosyl-1H-indol-3-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate

There total 3 articles about (S)-tert-butyl 4-(2-(2-(tert-butyldimethylsilyl)-1-tosyl-1H-indol-3-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate 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: 52.0%

(S)-tert-butyl 4-(4-(tert-butyldimethylsilyl)but-3-ynyl)-2,2-dimethyloxazolidine-3-carboxylate (1350542-06-1) + N-tosyl-2-iodoaniline (61613-20-5) → (S)-tert-butyl 4-(2-(2-(tert-butyldimethylsilyl)-1-tosyl-1H-indol-3-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate (1350542-14-1)

Guidance literature:

With palladium diacetate; sodium carbonate; lithium chloride; In N,N-dimethyl-formamide; at 80 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2011.10.055

Reference yield:

(S)-tert-butyl 4-(but-3-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1350542-20-9) → (S)-tert-butyl 4-(2-(2-(tert-butyldimethylsilyl)-1-tosyl-1H-indol-3-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate (1350542-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

1.2: -78 - 25 °C / Inert atmosphere

2.1: palladium diacetate; sodium carbonate; lithium chloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

With n-butyllithium; palladium diacetate; sodium carbonate; lithium chloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2011.10.055

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (S)-tert-butyl 4-(2-(2-(tert-butyldimethylsilyl)-1-tosyl-1H-indol-3-yl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate (1350542-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

1.2: -78 - 25 °C / Inert atmosphere

2.1: palladium diacetate; sodium carbonate; lithium chloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

With n-butyllithium; palladium diacetate; sodium carbonate; lithium chloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2011.10.055

upstream raw materials:

(S)-tert-butyl 4-(but-3-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

(S)-tert-butyl 4-(4-(tert-butyldimethylsilyl)but-3-ynyl)-2,2-dimethyloxazolidine-3-carboxylate

N-tosyl-2-iodoaniline

tert-butyldimethylsilyl chloride

Downstream raw materials:

(S)-tert-butyl 2,2-dimethyl-4-(2-(1-tosyl-1H-indol-3-yl)ethyl)oxazolidine-3-carboxylate

tert-butyl (S)-1-hydroxy-4-(1-tosyl-1H-indol-3-yl)butan-2-ylcarbamate

tert-butyl (S)-1-(methoxycarbonyl)-3-(1-tosyl-1H-indol-3-yl)propylcarbamate