Pentanamide, N,N,3-trimethyl-, (3S)- (9CI)

Base Information

• Chemical Name: Pentanamide, N,N,3-trimethyl-, (3S)- (9CI)
• CAS No.: 398453-86-6
• Molecular Formula: C₈H₁₇NO
• Molecular Weight: 143.229
• Mol file: 398453-86-6.mol

Synonyms:Pentanamide, N,N,3-trimethyl-, (3S)- (9CI)

Chemical Property of Pentanamide, N,N,3-trimethyl-, (3S)- (9CI)

Chemical Property:

• Boiling Point: 95 °C (17 mmHg)
• PSA: 20.31000
• LogP: 1.51080

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pentanamide, N,N,3-trimethyl-, (3S)- (9CI)

There total 5 articles about Pentanamide, N,N,3-trimethyl-, (3S)- (9CI) 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: 87.0%

(3S)-methylvaleric acid (1730-92-3) + dimethyl amine (124-40-3) → (S)-N,N-dimethyl-3-methylpentanamide (398453-86-6)

Guidance literature:

(3S)-methylvaleric acid; With thionyl chloride; In diethyl ether; for 5h; Heating;

dimethyl amine; In diethyl ether; at 20 ℃; for 24h; Further stages.;

DOI:10.1002/1099-0690(200111)2001:22<4321::AID-EJOC4321>3.0.CO;2-T

Reference yield: 79.0%

(E)-N,N-dimethylcrotonamide (14064-75-6) + ethylmagnesium bromide (925-90-6) → (S)-N,N-dimethyl-3-methylpentanamide (398453-86-6)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; C₂H₆O*C₃₆H₄₄FeP₂; boron trifluoride diethyl etherate; In diethyl ether; dichloromethane; at -78 ℃; for 18h; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.7b07344

Reference yield:

(E)-N,N-dimethylcrotonamide (14064-75-6) + ethylmagnesium bromide (925-90-6) → (R)-N,N-dimethyl-3-methylpentanamide (1051483-41-0) + (S)-N,N-dimethyl-3-methylpentanamide (398453-86-6)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; In diethyl ether; at -50 ℃; for 2h; Title compound not separated from byproducts.;

DOI:10.1016/j.tetasy.2008.06.017

upstream raw materials:

(3S)-methylvaleric acid

dimethyl amine

(S)-(2-methylbutyl)magnesium chloride

(E)-(-)-(1'R,2'R)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)but-2-enamide

Downstream raw materials:

(+)-(S)-3-methyl-1-pentene

(S)-N,N-dimethyl-3-methylpentylamine

Refernces

• 1、 Biswas, Kallolmay,Woodward, Simon. "Stereoselective 1,4-addition of Grignard reagents to α,β-enamides using a combined chiral auxiliary-catalyst approach". . p. 1702 - 1708. Retrieved 2008/12/21.