(Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide

Base Information

• Chemical Name: (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide
• CAS No.: 1312719-13-3
• Molecular Formula: C₁₉H₃₅NO₃SSi
• Molecular Weight: 385.643
• Mol file: 1312719-13-3.mol

Synonyms:(Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide

Chemical Property of (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide

There total 4 articles about (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide 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: 70.0%

(Rs)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethylidene)-2-methylpropane-2-sulfinamide (1312719-01-9) → (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide (1312719-13-3)

Guidance literature:

(Rs)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethylidene)-2-methylpropane-2-sulfinamide; With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 1h;

With water; In tetrahydrofuran; toluene; at -78 - 20 ℃; optical yield given as %de; diastereoselective reaction;

DOI:10.1016/j.tetasy.2011.01.011

Reference yield:

N-methoxy-N-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)acetamide (163089-34-7) → (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide (1312719-13-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.67 h / 20 °C / Inert atmosphere

1.2: 3 h / 0 °C / Inert atmosphere

2.1: titanium(IV) isopropylate / tetrahydrofuran / Inert atmosphere; Reflux

3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1 h / -78 °C

3.2: -78 - 20 °C

With titanium(IV) isopropylate; diisobutylaluminium hydride; magnesium; ethylene dibromide; In tetrahydrofuran; toluene;

DOI:10.1016/j.tetasy.2011.01.011

Reference yield:

3-methoxyphenyl bromide (2398-37-0) → (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide (1312719-13-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.67 h / 20 °C / Inert atmosphere

1.2: 3 h / 0 °C / Inert atmosphere

2.1: titanium(IV) isopropylate / tetrahydrofuran / Inert atmosphere; Reflux

3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1 h / -78 °C

3.2: -78 - 20 °C

With titanium(IV) isopropylate; diisobutylaluminium hydride; magnesium; ethylene dibromide; In tetrahydrofuran; toluene;

DOI:10.1016/j.tetasy.2011.01.011

upstream raw materials:

N-methoxy-N-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)acetamide

(Rs)-N-(2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethylidene)-2-methylpropane-2-sulfinamide

2-(tert-butyldimethylsilyloxy)-1-(3-methoxyphenyl)ethanone

3-methoxyphenyl bromide

Downstream raw materials:

(S)-2-amino-2-(3-methoxyphenyl)ethanol