N-tert-butoxycarbonyl-N-[(2-phenyldimethylsilyl)prop-2-enyl]benzylamine

Base Information

• Chemical Name: N-tert-butoxycarbonyl-N-[(2-phenyldimethylsilyl)prop-2-enyl]benzylamine
• CAS No.: 320618-79-9
• Molecular Formula: C₂₃H₃₁NO₂Si
• Molecular Weight: 381.59

Synonyms:N-tert-butoxycarbonyl-N-[(2-phenyldimethylsilyl)prop-2-enyl]benzylamine

Chemical Property of N-tert-butoxycarbonyl-N-[(2-phenyldimethylsilyl)prop-2-enyl]benzylamine

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Technology Process of N-tert-butoxycarbonyl-N-[(2-phenyldimethylsilyl)prop-2-enyl]benzylamine

There total 2 articles about N-tert-butoxycarbonyl-N-[(2-phenyldimethylsilyl)prop-2-enyl]benzylamine 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:

(dimethylphenylsilyl)acetylene (17156-64-8) → N-tert-butoxycarbonyl-N-[(2-phenyldimethylsilyl)prop-2-enyl]benzylamine (320618-79-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DIBAL / diethyl ether / 1 h / Heating

1.2: MeLi / tetrahydrofuran; diethyl ether / 0 - 20 °C

1.3: 71 percent / tetrahydrofuran; diethyl ether / 14 h / 20 °C

2.1: 89 percent / Br₂; triphenylphosphine; triethylamine / CH₂Cl₂ / 0.17 h / -20 °C

3.1: KH / tetrahydrofuran / 1 h / 0 °C

3.2: 83 percent / tetrahydrofuran / 14 h / 20 °C

With bromine; potassium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo0056343

Reference yield:

2-(dimethyl(phenyl)silyl)prop-2-en-1-ol (101844-22-8) → N-tert-butoxycarbonyl-N-[(2-phenyldimethylsilyl)prop-2-enyl]benzylamine (320618-79-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / Br₂; triphenylphosphine; triethylamine / CH₂Cl₂ / 0.17 h / -20 °C

2.1: KH / tetrahydrofuran / 1 h / 0 °C

2.2: 83 percent / tetrahydrofuran / 14 h / 20 °C

3.1: 78 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 - -40 °C

With n-butyllithium; bromine; potassium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; 3.1: aza-(2,3)-Wittig sigmatropic rearrangement;

DOI:10.1021/jo0056343

Reference yield: 78.0%

N-tert-butoxycarbonyl-N-[(2-phenyldimethylsilyl)prop-2-enyl]benzylamine (320618-79-9) → (1RS)-N-tert-butoxycarbonyl-1-phenyl-3-(phenyldimethylsilyl)-but-3-enamine

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 - -40 ℃;

DOI:10.1021/jo0056343

upstream raw materials:

(dimethylphenylsilyl)acetylene

2-(dimethyl(phenyl)silyl)prop-2-en-1-ol

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