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(1R,5S)-1-phenyl-3-azabicyclo[3.1.0]hexan-2-one, also known as Milnacipran impurity, is a chemical compound derived from the synthesis of Milnacipran (M344600), an antidepressant medication. It is characterized by its unique bicyclic structure and plays a role in the pharmaceutical industry due to its association with Milnacipran.

153275-06-0

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153275-06-0 Usage

Uses

Used in Pharmaceutical Industry:
(1R,5S)-1-phenyl-3-azabicyclo[3.1.0]hexan-2-one is used as an impurity in the production of Milnacipran, an antidepressant medication. It is significant for the pharmaceutical industry as it is associated with the development and manufacturing process of Milnacipran, which is a selective norepinephrine and serotonin reuptake inhibitor. This dual-action mechanism makes Milnacipran effective in managing fibromyalgia, a chronic pain disorder.
Additionally, understanding the properties and effects of (1R,5S)-1-phenyl-3-azabicyclo[3.1.0]hexan-2-one as an impurity can help in optimizing the synthesis process, ensuring the quality, safety, and efficacy of Milnacipran as a therapeutic agent for patients suffering from fibromyalgia and potentially other conditions that may benefit from its dual reuptake inhibition properties.

Check Digit Verification of cas no

The CAS Registry Mumber 153275-06-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,3,2,7 and 5 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 153275-06:
(8*1)+(7*5)+(6*3)+(5*2)+(4*7)+(3*5)+(2*0)+(1*6)=120
120 % 10 = 0
So 153275-06-0 is a valid CAS Registry Number.

153275-06-0Downstream Products

153275-06-0Relevant academic research and scientific papers

Preparation of Novel Lipophilic GABA Analogues Containing Cyclopropane Rings via Cyclopropanation of N-Silylated Unsaturated Amines

Paulini, Klaus,Reissig, Hans-Ulrich

, p. 55 - 59 (1995)

Novel lipophilic γ-amino acids 8 and 9 analogous to GABA containing cyclopropane rings are synthesized by Rh(II)-catalyzed reaction of diazo compounds 2 and 3 with N,N-bis(trimethylsilyl)allylamine (1) and subsequent hydrolysis.In addition, routes are des

Stereoselective construction of fused cyclopropane from ynamide and its application to synthesis of small drug candidate molecules

Ito, Tsubasa,Takenaka, Hiroki,Homma, Haruka,Harada, Shingo,Nemoto, Tetsuhiro

supporting information, (2021/04/09)

Herein, we report the development of an asymmetric intramolecular cyclopropanation reaction under silver catalysis. The strategy is based on diazo-free silver–carbene generation, providing γ-lactam fused cyclopropane in an enantioenriched form. The ring s

Copper(I)-Catalyzed Enyne Oxidation/Cyclopropanation: Divergent and Enantioselective Synthesis of Cyclopropanes

Shen, Wen-Bo,Tang, Xiang-Ting,Zhang, Ting-Ting,Lv, Dong-Can,Zhao, Dan,Su, Tong-Fu,Meng, Lei

, p. 1285 - 1290 (2021/02/20)

An efficient copper(I)-catalyzed enyne oxidation/cyclopropanation for the modular synthesis of cyclopropane derivatives is described, which represents the first non-noble metal-catalyzed enynes oxidation/cyclopropanation by the in situ generated α-oxo copper carbenes. This protocol allows the assembly of valuable cyclopropane-γ-lactams in generally good to excellent yields with excellent diastereoselectivity. More significantly, the enantioselective version of enyne oxidation/cyclopropanation has been disclosed with chiral copper catalysts.

Preparation method of levomilnacipran hydrochloride impurity

-

, (2020/09/16)

The invention relates to synthesis of impurities in medicines, and provides a preparation method for synthesizing levomilnacipran hydrochloride impurities. According to the method, benzyl cyanide andR-epoxy chloropropane are used as starting materials, primary amine is synthesized through substitution, chlorination and Gabriel, and cyan is hydrolyzed and subjected to ring closing. The levomilnacipran hydrochloride impurity can be obtained. The research on related substances of levomilnacipran hydrochloride is facilitated.

Synthesis of 3-aza-bicyclo[3.1.0]hexan-2-one derivatives via gold-catalyzed oxidative cyclopropanation of N -allylynamides

Wang, Kai-Bing,Ran, Rui-Qiao,Xiu, Shi-Dong,Li, Chuan-Ying

, p. 2374 - 2377 (2013/06/27)

N-Allylynamides with various functional groups and different substitution patterns can be converted into 3-aza-bicyclo[3.1.0]hexan-2-one derivatives in moderate to high yield using IMesAuCl/AgBF4 as the catalyst and pyridine N-oxide as the oxidant. A noncarbene mediated approach is proposed as the mechanism.

Studies on the structure-activity relationship of bicifadine analogs as monoamine transporter inhibitors

Zhang, Mingzhu,Jovic, Florence,Vickers, Troy,Dyck, Brian,Tamiya, Junko,Grey, Jonathan,Tran, Joe A.,Fleck, Beth A.,Pick, Rebecca,Foster, Alan C.,Chen, Chen

scheme or table, p. 3682 - 3686 (2009/04/06)

Compounds with various activities and selectivities were discovered through structure-activity relationship studies of bicifadine analogs as monoamine transporter inhibitors. The norepinephrine-selective 2-thienyl compound S-6j was efficacious in a rodent

Phenyl azabicyclohexanones

-

, (2008/06/13)

Substituted phenyl azabicyclohexanones, their method of preparation, and their conversion into substituted phenyl azabicyclohexanes which are active anxiolytic and analgesic agents.

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