Cyclopropanecarboxamide, N,N-diethyl-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-phenyl-, (1R,2S)-rel-

Base Information

• Chemical Name: Cyclopropanecarboxamide, N,N-diethyl-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-phenyl-, (1R,2S)-rel-
• CAS No.: 923037-67-6
• Molecular Formula: C₂₂H₂₇NO₄S
• Molecular Weight: 401.527
• Mol file: 923037-67-6.mol

Synonyms:

Chemical Property of Cyclopropanecarboxamide, N,N-diethyl-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-phenyl-, (1R,2S)-rel-

Chemical Property:

• PSA: 72.06000
• LogP: 4.60740

Purity/Quality:

(1R,2S)-rel-N,N-Diethyl-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-phenyl-cyclopropanecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (1R,2S)-rel-N,N-Diethyl-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-phenyl-cyclopropanecarboxamide is an intermediate in synthesizing rac,trans-Milnacipran Hydrochloride (M344625), which is an impurity of rac-Milnacipran Hydrochloride (M344600), an antidepressant and a selective norepinephrine and serotonin reuptake inhibitor.

Technology Process of Cyclopropanecarboxamide, N,N-diethyl-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-phenyl-, (1R,2S)-rel-

There total 7 articles about Cyclopropanecarboxamide, N,N-diethyl-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-phenyl-, (1R,2S)-rel- 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: 91.7%

p-toluenesulfonyl chloride (98-59-9) + (1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide (172015-99-5) → C22H27NO4S (923037-67-6)

Guidance literature:

In toluene; at 0 - 20 ℃; for 2h;

Reference yield: 80.5%

toluene-p-sulfonyl bromide (1950-69-2) + (1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide (172015-99-5) → C22H27NO4S (923037-67-6)

Guidance literature:

In toluene; at 0 - 20 ℃; for 2h;

Reference yield:

(1R,2R)-2-Acetoxymethyl-1-phenyl-cyclopropanecarboxylic acid → Toluene-4-sulfonic acid (1R,2R)-2-diethylcarbamoyl-2-phenyl-cyclopropylmethyl ester (923037-67-6)

Guidance literature:

Multi-step reaction with 4 steps

1: SOCl₂

2: ethanol / Ambient temperature

3: NaOH

4: pyridine / 15 h / 5 °C

With pyridine; sodium hydroxide; thionyl chloride; In ethanol;

DOI:10.1021/jm00385a013

upstream raw materials:

(1R,2R)-2-Hydroxymethyl-1-phenyl-cyclopropanecarboxylic acid diethylamide

p-toluenesulfonyl chloride

(1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide

toluene-p-sulfonyl bromide

Refernces

• 1、 Bonnaud, Bernard,Cousse, Henri,Mouzin, Gilbert,Briley, Mike,Stenger, Antoine,et al.. "1-Aryl-2-(aminomethyl)cyclopropanecarboxylic Acid Derivatives. A New Series of Potential Antidepressants". . p. 318 - 325. Retrieved 2007/10/02.