Solifenacin Succinate EP Impurity H

Base Information

• Chemical Name: Solifenacin Succinate EP Impurity H
• CAS No.: 732228-02-3
• Molecular Formula: C₂₃H₂₆N₂O₂
• Molecular Weight: 362.472
• European Community (EC) Number: 826-250-8
• UNII: JXA63E787Z
• ChEMBL ID: CHEMBL606902
• Mol file: 732228-02-3.mol

Synonyms:732228-02-3;Solifenacin Succinate EP Impurity H;(1S,3'S)-Solifenacin;JXA63E787Z;(S)-Quinuclidin-3-yl (S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate;2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-1-phenyl-, (3S)-1-azabicyclo(2.2.2)oct-3-yl ester, (1S)-;UNII-JXA63E787Z;CHEMBL606902;SCHEMBL1735770;FBOUYBDGKBSUES-YADHBBJMSA-N;Solifenacin succinate impurity H [EP];EN300-27693669;SOLIFENACIN SUCCINATE IMPURITY H [EP IMPURITY];(3r)-1-azabicyclo[2.2.2]oct-3-yl (1s)-3,4-dihydro-1-phenyl-2(1h)-isoquinolinecarboxylate;(1S)-(3S)-1-azabicyclo[2.2.2]oct-3-yl 3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate;(3S)-1-azabicyclo[2.2.2]octan-3-yl (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate;[(3S)-1-azabicyclo[2.2.2]octan-3-yl] (1S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate

Chemical Property of Solifenacin Succinate EP Impurity H

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 362.199428076
• Heavy Atom Count: 27
• Complexity: 525

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CCC1C(C2)OC(=O)N3CCC4=CC=CC=C4C3C5=CC=CC=C5
• Isomeric SMILES: C1CN2CCC1[C@@H](C2)OC(=O)N3CCC4=CC=CC=C4[C@@H]3C5=CC=CC=C5
• Uses: (1S,3S)-Solifenacin is an intermediate used in the synthesis of (1S,3’S)-Solifenacin Succinate (S676730), which is a muscarinic M3 receptor antagonist and used in treatment of urinary incontinence.

Technology Process of Solifenacin Succinate EP Impurity H

There total 13 articles about Solifenacin Succinate EP Impurity H 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: 1.1%

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline (180468-42-2) + (R)-quinuclidin-3-ol (25333-42-0) → (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester (732228-02-3,180272-14-4) + (3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate (740780-79-4,180272-14-4) + (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8,96719-89-0,118864-75-8) + solifenacin (242478-37-1,180272-14-4)

Guidance literature:

With potassium 2-methylbutan-2-olate; In toluene; at 90 ℃; for 3h; Product distribution / selectivity;

Reference yield:

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline (180468-42-2) + 3-quinuclidinol (1619-34-7) → (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester (732228-02-3,180272-14-4) + solifenacin (242478-37-1,180272-14-4)

Guidance literature:

With sodium hydride; In toluene; mineral oil; at 25 - 30 ℃; for 24h; Product distribution / selectivity; Inert atmosphere; Reflux;

Reference yield:

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline (180468-42-2) → (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester (732228-02-3,180272-14-4) + (3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate (740780-79-4,180272-14-4) + solifenacin (242478-37-1,180272-14-4)

Guidance literature:

(R)-quinuclidin-3-ol; With sodium hydride; In toluene; for 0.166667h;

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline; In toluene; at 26 - 110 ℃; for 4.33333h; Product distribution / selectivity;

upstream raw materials:

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

(S)-quinuclidin-3-ol

1-phenyl-3,4-dihydroisoquinoline

N-phenethylbenzamide

Downstream raw materials:

(3R)-1-azabicyclo[2.2.2]oct-3-yl (1S)-3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate hydrogen L-tartrate

(1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester succinate

(3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate succinate

solifenacin succinate

Refernces

• 1、 -. "NOVEL PROCESS FOR THE PREPARATION OF SOLIFENACIN SUCCINATE". Paragraph 0034; 0035; 0036. . Retrieved 2013/05/22.
• 2、 Niphade, Navnath C.,Jagtap, Kunal M.,Mali, Anil C.,Solanki, Pavankumar V.,Jachak, Madhukar N.,Mathad, Vijayavitthal T.. "Efficient and single pot process for the preparation of enantiomerically pure solifenacin succinate, an antimuscarinic agent". body text. p. 1181 - 1186. Retrieved 2012/01/06.