(E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine

Base Information

• Chemical Name: (E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine
• CAS No.: 1286169-82-1
• Molecular Formula: C₂₀H₂₉NO₅
• Molecular Weight: 363.454
• Mol file: 1286169-82-1.mol

Synonyms:(E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine

Chemical Property of (E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine

There total 4 articles about (E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine 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: 83.0%

1-bromo-4-methoxy-benzene (104-92-7) + N,N-bis(tert-butoxycarbonyl)allylamine (115269-99-3) → (E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine (1286169-82-1)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; palladium diacetate; potassium carbonate; In water; at 90 ℃; for 3h; regioselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201100835

Reference yield:

4-methoxybenzenediazonium tetrafluoroborate (459-64-3) + N,N-bis(tert-butoxycarbonyl)allylamine (115269-99-3) → (E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine (1286169-82-1)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium acetate; In benzonitrile; at 20 ℃; optical yield given as %de; stereoselective reaction;

DOI:10.1021/jo201105z

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine (1286169-82-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / ethanol / 1 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 - 0 °C / Inert atmosphere

2.2: 1 h / -78 - 20 °C / Inert atmosphere

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium acetate / benzonitrile / 20 °C

With 1H-imidazole; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; sodium acetate; In tetrahydrofuran; ethanol; benzonitrile; 3.1: Heck-Matsuda reaction;

DOI:10.1021/jo201105z

upstream raw materials:

di-tert-butyl dicarbonate

N-tert-butoxycarbonylprop-2-en-1-amine

4-methoxybenzenediazonium tetrafluoroborate

N,N-bis(tert-butoxycarbonyl)allylamine