(S)-tert-butyl (1-(4-methoxyphenyl)penta-3,4-dien-2-yl)carbamate

Base Information

• Chemical Name: (S)-tert-butyl (1-(4-methoxyphenyl)penta-3,4-dien-2-yl)carbamate
• CAS No.: 1310480-41-1
• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.375
• Mol file: 1310480-41-1.mol

Synonyms:(S)-tert-butyl (1-(4-methoxyphenyl)penta-3,4-dien-2-yl)carbamate

Chemical Property of (S)-tert-butyl (1-(4-methoxyphenyl)penta-3,4-dien-2-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl (1-(4-methoxyphenyl)penta-3,4-dien-2-yl)carbamate

There total 10 articles about (S)-tert-butyl (1-(4-methoxyphenyl)penta-3,4-dien-2-yl)carbamate 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: 66.0%

4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane (865350-17-0) + tert-butyl (2-(4-methoxyphenyl)ethylidene)carbamate (1572519-69-7) → (S)-tert-butyl (1-(4-methoxyphenyl)penta-3,4-dien-2-yl)carbamate (1310480-41-1)

Guidance literature:

With sodium t-butanolate; In ethanol; toluene; at 22 ℃; for 14h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja500374p

Reference yield: 60.0%

(2S)-N-(tert-butoxycarbonyl)-1-(4-methoxyphenyl)but-3-yn-2-amine + formaldehyd (50-00-0,30525-89-4,61233-19-0) → (S)-tert-butyl (1-(4-methoxyphenyl)penta-3,4-dien-2-yl)carbamate (1310480-41-1)

Guidance literature:

With copper(l) iodide; diisopropylamine; In 1,4-dioxane; for 21h; Reflux;

DOI:10.1002/chem.201003727

Reference yield:

4-Methoxyphenylacetaldehyde (5703-26-4) → (S)-tert-butyl (1-(4-methoxyphenyl)penta-3,4-dien-2-yl)carbamate (1310480-41-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 2 h / 0 °C

2.1: dmap; triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

3.1: 2,6-bis[(4S)-4-methyl-4,5-dihydrooxazol-2-yl]pyridine; copper(l) iodide / methanol / 18 - 25 °C

3.2: 72 h / 18 - 25 °C

4.1: [bis(acetoxy)iodo]benzene / methanol; acetonitrile / 2 h / 20 °C

4.2: 1.5 h

5.1: potassium carbonate / dichloromethane / 17 h / 20 °C / pH 11

6.1: copper(l) iodide; diisopropylamine / 1,4-dioxane / 21 h / Reflux

With 2,6-bis[(4S)-4-methyl-4,5-dihydrooxazol-2-yl]pyridine; dmap; copper(l) iodide; [bis(acetoxy)iodo]benzene; potassium carbonate; triethylamine; diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetonitrile; 6.1: Crabbe reaction;

DOI:10.1002/chem.201003727

upstream raw materials:

formaldehyd

(S)-2-methoxy-N-(1-(4-methoxyphenyl)but-3-yn-2-yl)aniline

1-(4-methoxyphenyl)but-3-yn-2-yl pivalate

4-Methoxyphenylacetaldehyde

Downstream raw materials:

(S)-tert-butyl 2-(4-methoxybenzyl)-2,5-dihydro-1H-pyrrole-1-carboxylate