(R)-N-methyl-N-methoxy-3-(4-methylphenyl)butanamide

Base Information

• Chemical Name: (R)-N-methyl-N-methoxy-3-(4-methylphenyl)butanamide
• CAS No.: 848674-84-0
• Molecular Formula: C₁₃H₁₉NO₂
• Molecular Weight: 221.299
• Mol file: 848674-84-0.mol

Synonyms:(R)-N-methyl-N-methoxy-3-(4-methylphenyl)butanamide

Chemical Property of (R)-N-methyl-N-methoxy-3-(4-methylphenyl)butanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-methyl-N-methoxy-3-(4-methylphenyl)butanamide

There total 13 articles about (R)-N-methyl-N-methoxy-3-(4-methylphenyl)butanamide 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: 94.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (R)-3-(4-methylphenyl)butanoic acid (93922-52-2) → (R)-N-methyl-N-methoxy-3-(4-methylphenyl)butanamide (848674-84-0)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.3390/10091023

Reference yield:

4-methylphenylboronic acid (5720-05-8) + (E)-N-methoxy-N-methyl-2-butenamide (109480-79-7,121712-52-5) → N-methoxy-N-methyl-3-p-tolyl-butyramide + (R)-N-methyl-N-methoxy-3-(4-methylphenyl)butanamide (848674-84-0)

Guidance literature:

With potassium hydroxide; (1S,4S)-2,5-dibenzylbicyclo[2.2.1]cycloocta-2,5-diene; bis(ethylene)rhodium(I) chloride dimer; In 1,4-dioxane; at 50 ℃; for 20h; Title compound not separated from byproducts;

DOI:10.1039/b502921j

Reference yield:

para-bromotoluene (106-38-7) → (R)-N-methyl-N-methoxy-3-(4-methylphenyl)butanamide (848674-84-0)

Guidance literature:

Multi-step reaction with 2 steps

1: B(OMe)3

2: aq. KOH; (1S,4S)-2,5-dibenzylbicyclo[2.2.1]cycloocta-2,5-diene / [RhCl(C₂H₄)2]2 / dioxane / 20 h / 50 °C

With potassium hydroxide; Trimethyl borate; (1S,4S)-2,5-dibenzylbicyclo[2.2.1]cycloocta-2,5-diene; bis(ethylene)rhodium(I) chloride dimer; In 1,4-dioxane;

DOI:10.1039/b502921j

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

(R)-3-(4-methylphenyl)butanoic acid

4-methylphenylboronic acid

(E)-N-methoxy-N-methyl-2-butenamide

Downstream raw materials:

(R)-2-methyl-6-(4-methylphenyl)-2-hepten-4-one

Refernces

• 1、 Mori, Kenji. "Organic synthesis in pheromone science". . p. 1023 - 1047. Retrieved 2007/10/03.
• 2、 Shintani, Ryo,Kimura, Takahiro,Hayashi, Tamio. "Rhodium/diene-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated Weinreb amides". . p. 3213 - 3214. Retrieved 2007/10/03.