[2R,3S,1'S,2'S]-(+)-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2,5-trimethylpentanamide

Base Information

• Chemical Name: [2R,3S,1'S,2'S]-(+)-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2,5-trimethylpentanamide
• CAS No.: 219783-14-9
• Molecular Formula: C₁₇H₂₇NO₃
• Molecular Weight: 293.406
• Mol file: 219783-14-9.mol

Synonyms:[2R,3S,1'S,2'S]-(+)-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2,5-trimethylpentanamide

Chemical Property of [2R,3S,1'S,2'S]-(+)-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2,5-trimethylpentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2R,3S,1'S,2'S]-(+)-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2,5-trimethylpentanamide

There total 1 articles about [2R,3S,1'S,2'S]-(+)-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2,5-trimethylpentanamide 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%

isobutyraldehyde (78-84-2) + N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3) → [2R,3S,1'S,2'S]-(+)-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2,5-trimethylpentanamide (219783-14-9)

Guidance literature:

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃;

With zirconocene dichloride; In tetrahydrofuran; at -78 ℃; for 1h;

isobutyraldehyde; In tetrahydrofuran; at -105 ℃; for 2.33333h; Further stages.;

DOI:10.1021/jo000035h

Reference yield: 98.0%

[2R,3S,1'S,2'S]-(+)-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2,5-trimethylpentanamide (219783-14-9) → pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) + (+)-(2R,3S)-3-hydroxy-2,4-dimethylpentanoic acid (77341-63-0)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; for 2h; Heating;

DOI:10.1021/jo000035h

Reference yield: 69.0%

phenyllithium (591-51-5) + [2R,3S,1'S,2'S]-(+)-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2,5-trimethylpentanamide (219783-14-9) → [2R,3S]-(+)-3-hydroxy-2,4-dimethyl-1-phenyl-1-pentanone (283151-94-0)

Guidance literature:

phenyllithium; [2R,3S,1'S,2'S]-(+)-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2,5-trimethylpentanamide; In tetrahydrofuran; at -78 - 0 ℃; for 0.416667h;

With diisopropylamine; In tetrahydrofuran; for 0.25h; Further stages.;

DOI:10.1021/jo000035h

upstream raw materials:

isobutyraldehyde

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide

Downstream raw materials:

[2R,3S]-(+)-3-hydroxy-2,4-dimethyl-1-phenyl-1-pentanone

pseudoephedrine

(+)-(2R,3S)-3-hydroxy-2,4-dimethylpentanoic acid

Refernces

• 1、 Vicario, Jose L.,Badia, Dolores,Dominguez, Esther,Rodriguez, Monica,Carrillo, Luisa. "Asymmetric aldol reactions using (S,S)-(+)-pseudoephedrine-based amides: Stereoselective synthesis of α-methyl-β-hydroxy acids, esters, ketones, and 1,3-syn and 1,3-anti diols". . p. 3754 - 3759. Retrieved 2007/10/03.