(S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylindoline

Base Information

• Chemical Name: (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylindoline
• CAS No.: 1365533-56-7
• Molecular Formula: C₂₂H₃₁NO₃SSi
• Molecular Weight: 417.645
• Mol file: 1365533-56-7.mol

Synonyms:(S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylindoline

Chemical Property of (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylindoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylindoline

There total 10 articles about (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylindoline 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: 97.0%

(S)-N-(1-(2-bromophenyl)-3-((tert-butyldimethylsilyl)oxy)propan-2-yl)-p-toluenesulfonamide (1365533-55-6) → (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylindoline (1365533-56-7)

Guidance literature:

With palladium diacetate; potassium carbonate; methyl vinyl ketone; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 110 ℃; for 16h;

DOI:10.1016/j.tetlet.2012.01.037

Reference yield:

(S)-N-(1-(2-bromophenyl)-3-((tert-butyldimethylsilyl)oxy)propan-2-yl)-p-toluenesulfonamide (1365533-55-6) → (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylindoline (1365533-56-7) + 1-((1R,3S)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-tosyl-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-one (1365533-66-9) + 1-((1S,3S)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-tosyl-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-one (1365533-58-9)

Guidance literature:

With palladium diacetate; potassium carbonate; methyl vinyl ketone; triphenylphosphine; In toluene; at 110 ℃; for 16h; optical yield given as %de; diastereoselective reaction;

DOI:10.1016/j.tetlet.2012.01.037

Reference yield:

2-bromo-L-phenylalanine methyl ester (938069-18-2) → (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylindoline (1365533-56-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 16 h / 20 °C

2.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 16 h / 0 - 20 °C

2.2: 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

4.1: palladium diacetate; potassium carbonate; methyl vinyl ketone; tri tert-butylphosphoniumtetrafluoroborate / toluene / 16 h / 110 °C

With 1H-imidazole; sodium tetrahydroborate; palladium diacetate; potassium carbonate; methyl vinyl ketone; triethylamine; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Buchwald-Hartwig cross-coupling;

DOI:10.1016/j.tetlet.2012.01.037

upstream raw materials:

2-bromo-L-phenylalanine methyl ester

(S)-methyl 3-(2-bromophenyl)-2-(p-toluenylsulfonamido)propanoate

(S)-N-(1-(2-bromophenyl)-3-((tert-butyldimethylsilyl)oxy)propan-2-yl)-p-toluenesulfonamide

p-toluenesulfonyl chloride

Refernces