N-[2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethyl]-acetamide

Base Information

• Chemical Name: N-[2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethyl]-acetamide
• CAS No.: 257300-02-0
• Molecular Formula: C₁₉H₃₃NO₄Si
• Molecular Weight: 367.561
• Mol file: 257300-02-0.mol

Synonyms:N-[2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethyl]-acetamide

Chemical Property of N-[2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethyl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethyl]-acetamide

There total 5 articles about N-[2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethyl]-acetamide 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: 99.0%

acetic anhydride (108-24-7) + 2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethylamine (228704-10-7) → N-[2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethyl]-acetamide (257300-02-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

Reference yield:

1-chloro-3,5-dimethoxybenzene (7051-16-3) → N-[2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethyl]-acetamide (257300-02-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Mg; BrCH₂CH₂Br / tetrahydrofuran / 10 h / Heating

1.2: 92 percent / CuBr*SMe₂ / tetrahydrofuran / 4.5 h / -20 °C

2.1: 88 percent / PPh₃; DEAD / tetrahydrofuran / 20 h / 0 - 20 °C

3.1: 89 percent / H₂NNH₂ / ethanol / 7 h / Heating

4.1: 99 percent / NEt₃ / CH₂Cl₂ / 20 °C

With magnesium; ethylene dibromide; triethylamine; triphenylphosphine; hydrazine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Metallation / 1.2: Ring cleavage / 2.1: Mitsunobu reaction / 3.1: Hydrazinolysis / 4.1: Acetylation;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

Reference yield:

tert-butyldimethylsilyl (S)-glycidyl ether (78906-15-7,114413-26-2,124150-87-4,123237-62-7) → N-[2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethyl]-acetamide (257300-02-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Mg; BrCH₂CH₂Br / tetrahydrofuran / 10 h / Heating

1.2: 92 percent / CuBr*SMe₂ / tetrahydrofuran / 4.5 h / -20 °C

2.1: 88 percent / PPh₃; DEAD / tetrahydrofuran / 20 h / 0 - 20 °C

3.1: 89 percent / H₂NNH₂ / ethanol / 7 h / Heating

4.1: 99 percent / NEt₃ / CH₂Cl₂ / 20 °C

With magnesium; ethylene dibromide; triethylamine; triphenylphosphine; hydrazine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Metallation / 1.2: Ring cleavage / 2.1: Mitsunobu reaction / 3.1: Hydrazinolysis / 4.1: Acetylation;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

upstream raw materials:

acetic anhydride

2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethylamine

1-chloro-3,5-dimethoxybenzene

tert-butyldimethylsilyl (S)-glycidyl ether

Downstream raw materials:

[(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol

(1R,3S)-6,8-Dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

C₃₂H₃₃INO₅PS