(1R,2R)-2-(3,4-difluorophenyl)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl acetamide

Base Information

• Chemical Name: (1R,2R)-2-(3,4-difluorophenyl)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl acetamide
• CAS No.: 440370-30-9
• Molecular Formula: C₁₈H₁₉F₂NO₂
• Molecular Weight: 319.351
• Mol file: 440370-30-9.mol

Synonyms:(1R,2R)-2-(3,4-difluorophenyl)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl acetamide

Chemical Property of (1R,2R)-2-(3,4-difluorophenyl)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-2-(3,4-difluorophenyl)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl acetamide

There total 2 articles about (1R,2R)-2-(3,4-difluorophenyl)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl acetamide 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%

(3,4-difluorophenyl)acetic acid (658-93-5) + (1R,2R)-pseudoephedrine (321-97-1,7009-81-6,90-83-5,6912-63-6) → (1R,2R)-2-(3,4-difluorophenyl)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl acetamide (440370-30-9)

Guidance literature:

With 2-hydroxy-pyridine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/jo0504161

Reference yield:

(3,4-difluorophenyl)acetic acid (658-93-5) → (1R,2R)-2-(3,4-difluorophenyl)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl acetamide (440370-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / dimethylformamide / 0 °C

2: 90 percent / aq. NaOH / isopropyl acetate / 16 h / 0 °C

With sodium hydroxide; thionyl chloride; In Isopropyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo035564a

Reference yield: 60.0%

(E)-4-(4-methoxy-phenoxy)-but-2-enoic acid methyl ester (96821-35-1) + (1R,2R)-2-(3,4-difluorophenyl)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl acetamide (440370-30-9) → 4-(R)-(3,4-difluorophenyl)-4-{N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylcarbamoyl}-3-(R)-(4-methoxyphenoxymethyl)butyric acid methyl ester (440370-41-2)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.666667h;

DOI:10.1021/ol0259847

upstream raw materials:

(3,4-difluorophenyl)acetic acid

(1R,2R)-pseudoephedrine

Downstream raw materials:

4-(R)-(3,4-difluorophenyl)-4-{N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylcarbamoyl}-3-(R)-(4-methoxyphenoxymethyl)butyric acid methyl ester

1-[3-(R)-(3,4-difluorophenyl)-2-hydroxytetrahydro-2H-pyran-4(R)-ylmethyl]-3-(R)-methylpiperidine-3-carboxylic acid ethyl ester

3-(R)-methyl-1-[2-oxo-3-(R)-(3,4-difluorophenyl)tetrahydro-2H-pyran-4(R)-ylmethyl]piperidine-3-carboxylic acid ethyl ester

1-[3-(R)-(3,4-difluorophenyl)-2-(4-nitrobenzoyloxy)tetrahydro-2H-pyran-4(R)-ylmethyl]-3-(R)-methylpiperidine-3-carboxylic acid ethyl ester

Refernces

• 1、 Smitrovich, Jacqueline H.,DiMichele, Lisa,Qu, Chuanxing,Boice, Genevieve N.,Nelson, Todd D.,Huffman, Mark A.,Murry, Jerry. "Michael Reactions of Pseudoephedrine Amide Enolates: Effect of LiCl on Syn/Anti Selectivity". . p. 1903 - 1908. Retrieved 2007/10/03.