1237261-65-2

Basic information

• Product Name: (1S,2R)-2-((1,3-dioxoisoindolin-2-yl)Methyl)-N,N-diethyl-1-phenylcyclopropanecarboxaMide
• Synonyms: (1S,2R)-2-((1,3-dioxoisoindolin-2-yl)Methyl)-N,N-diethyl-1-phenylcyclopropanecarboxaMide;(1S,2R)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide-cyclopropanecarboxamide
• CAS NO: 1237261-65-2
• Molecular Formula: C₂₃H₂₄N₂O₃
• Molecular Weight: 376.44826
• Mol File: 1237261-65-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S,2R)-2-((1,3-dioxoisoindolin-2-yl)Methyl)-N,N-diethyl-1-phenylcyclopropanecarboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-2-((1,3-dioxoisoindolin-2-yl)Methyl)-N,N-diethyl-1-phenylcyclopropanecarboxaMide(1237261-65-2)
• EPA Substance Registry System: (1S,2R)-2-((1,3-dioxoisoindolin-2-yl)Methyl)-N,N-diethyl-1-phenylcyclopropanecarboxaMide(1237261-65-2)

Safety Data

• Hazardous Substances Data: 1237261-65-2(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
(1S,2R)-2-((1,3-dioxoisoindolin-2-yl)Methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide is used as a building block or intermediate in the synthesis of pharmaceuticals due to its unique structural features and the biological activity associated with the isoindolin-1,3-dione moiety.
Used in Pharmaceutical Research:
In pharmaceutical research, (1S,2R)-2-((1,3-dioxoisoindolin-2-yl)Methyl)-N,N-diethyl-1-phenylcyclopropanecarboxaMide may serve as a template for the development of new drugs, given its potential to interact with biological targets due to its diverse functional groups and the presence of the bioactive isoindolin-1,3-dione core.
Used in Drug Design and Optimization:
(1S,2R)-2-((1,3-dioxoisoindolin-2-yl)Methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide can be utilized in the design and optimization of drugs targeting specific diseases, leveraging its structural diversity and the possibility of modifying its substituents to improve binding affinity and selectivity.
Used in Chemical Synthesis:
As a versatile chemical intermediate, (1S,2R)-2-((1,3-dioxoisoindolin-2-yl)Methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide may be employed in various chemical synthesis processes to produce a range of compounds with potential applications in different industries, including but not limited to pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 74-96-4 ethyl bromide 
• 923037-67-6 C₂₂H₂₇NO₄S 
• 1074-82-4 potassium phtalimide 
• 136918-14-4 phthalimide 
• 172015-99-5 (1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide 
• 22613-99-6 cis-2-Hydroxymethyl-1-phenyl-cyclopropan-1-carbonsaeure 
• 140-29-4 phenylacetonitrile 
• 63106-93-4 (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 1237261-60-7 (1S,2R)-2-(chloromethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide 

Downstream Products

• 96847-54-0 (1S,2R)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide 
• 101152-94-7 (1S,2R)-milnacipran hydrochloride 

Relevant articles and documents

Preparation method of levomilnacipran key intermediate

Levomilnacipran has a chemical name of (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide, is a medicine which is researched and developed by a French PierreFabre laboratory at the earliest time and is used for treating adult severe depre

Preparation of leveminacipran hydrochloride

The invention discloses a novel preparation method for synthesizing leveminacipran hydrochloride, and relates to a compound represented by a formula A. According to the invention, each step of reaction is simple in operation and mild in condition, use of

Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes

We herein report an Ir-catalyzed enantioselective C(sp3)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the first time. A variety of substrates with α-quaternary carbon centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. We have also demonstrated that the borylated products can be used as versatile precursors engaging in stereospecific transformations of C-B bonds, including the synthesis of a bioactive compound Levomilnacipran.

PROCESS FOR THE PREPARATION OF (1S,2R)-MILNACIPRAN

The invention relates to a process for the preparation of Levomilnacipran, a compound useful in the treatment of depression, comprising the following steps: a) directly converting the enantiomerically enriched form of alcohol (D) into the enantiomerically enriched form of the phthalimido derivative (C) by treatment with phthalimide in the presence of a trialkyl or triarylphosphine and of a dialkyl azodicarboxylate, formula (I) wherein the amount of phthalimide is comprised between 1 and 1.3 equivalents with respect to the molar amount of alcohol (D) used, and the amounts of both the phosphine and the azodicarboxylate are comprised, independently from each other, between 1 and 1.5 equivalents with respect to the molar amount of alcohol (D) used; b) deblocking the enantiomerically enriched form of the phthalimido derivative (C) to obtain Levomilnacipran, formula (II).

Preparation method of levomilnacipran hydrochloride

The invention provides a preparation method of levomilnacipran hydrochloride. According to the preparation method, a mixed liquid is obtained through a mixed reaction of a compound adopting the structure shown in the formula (II) and alkali; then acid is

COMPOSITIONS AND METHODS FOR THE TREATMENT OF NEUROLOGICAL CONDITIONS

The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of neurological conditions may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of fibromyalgia, depression, neuropathic pain, severe pain, chronic pain, generalized pain, injury, post-operative pain, osteoarthritis, rheumatoid arthritis, multiple sclerosis, spinal cord injury, migraine, HIV related neuropathic pain, post herpetic neuralgia, diabetic neuropathy, cancer pain, fibromyalgia and lower back pain.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF NEUROLOGICAL CONDITIONS

The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for the treatment of neurological conditions may he formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may he used to treatment: of fibromyalgia, depression, neuropathic pain, severe pain, chronic pain, generalized pain, injury, post-operative pain, osteoarthritis, rheumatoid arthritis, multipie sclerosis, spinal cord injury, migraine, HIV related neuropathic pain, post herpetic neuralgia, diabetic neuropathy, cancer pain, fibromyalgia and lower back pain.

Enantioselective synthesis of levomilnacipran

A novel approach for the asymmetric synthesis of the active (1S,2R)-enantiomer of the antidepressant milnacipran is reported. The two stereogenic centers borne by the cyclopropane ring were sequentially installed starting from phenylacetic acid.

METHOD FOR SYNTHESIS OF (1S, 2R)-MILNACIPRAN

The present invention relates to a method for synthesizing a pharmaceutically acceptable acid addition salt of (1S, 2R)-milnacipran comprising the following successive steps: (a) reaction of phenylacetonitrile and of (R)-epichlorhydrin in the presence of a base containing an alkaline metal, followed by a basic treatment, and then by an acid treatment in order to obtain a lactone; (b) reaction of said lactone with MNEt2, wherein M represents an alkaline metal, or with NHEt2 in the presence of a Lewis acid-amine complex, in order to obtain an amide-alcohol; (c) reaction of said amide-alcohol with thionyl chloride in order to obtain a chlorinated amide; (d) reaction of said chlorinated amide with a phthalimide salt in order to obtain a phthalimide derivative; (e) hydrolysis of the phthalimide group of said phthalimide derivative in order to obtain (1S, 2R)-milnacipran, and (f) salification of (1S, 2R)-milnacipran in a suitable solvent system in the presence of a pharmaceutically acceptable acid.