Esreboxetine

Base Information

• Chemical Name: Esreboxetine
• CAS No.: 98819-76-2
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.397
• UNII: L8S50ZY490
• DSSTox Substance ID: DTXSID601009938
• Nikkaji Number: J569.656I
• Wikipedia: Esreboxetine
• Wikidata: Q5399299
• NCI Thesaurus Code: C175719
• Pharos Ligand ID: C7VY6F2T6RYT
• Metabolomics Workbench ID: 42636
• ChEMBL ID: CHEMBL180101
• Mol file: 98819-76-2.mol

Synonyms:(+)-(2S)-2-((S)-(2-ethoxyphenoxy)phenylmethyl)morpholine;esreboxetine

Chemical Property of Esreboxetine

Chemical Property:

• PSA: 39.72000
• Density: 1.113 g/cm³
• LogP: 3.52260
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 313.16779360
• Heavy Atom Count: 23
• Complexity: 333

Purity/Quality:

98%Min ^*data from raw suppliers

(S,S)-Reboxetine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC=CC=C1OC(C2CNCCO2)C3=CC=CC=C3
• Isomeric SMILES: CCOC1=CC=CC=C1O[C@H]([C@@H]2CNCCO2)C3=CC=CC=C3
• Recent ClinicalTrials: Open Label Extension Study of [S,S]-Reboxetine in Patients With Fibromyalgia
• Recent EU Clinical Trials: Depressions-Spektrums-St?rung und differenzielle Effekte neuerer Antidepressiva auf die Verkehrssicherheit
• Uses: (S,S)-Reboxetine is a stereoisomer of Reboxetine (R142000, Mesylate), a selective noradrenaline reuptake inhibitor.

Technology Process of Esreboxetine

There total 108 articles about Esreboxetine 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:

(2RS,3RS)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one (93886-32-9,98769-79-0,98769-80-3,98819-75-1) → reboxetine (71620-89-8,71621-36-8,93851-86-6,98769-81-4,98769-83-6,98819-76-2,105017-38-7)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; for 4h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)96541-X

Reference yield:

trans-2,3-epoxy-3-phenylpropan-1-ol (40641-81-4) → reboxetine (71620-89-8,71621-36-8,93851-86-6,98769-81-4,98769-83-6,98819-76-2,105017-38-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaOH / 1.) H₂O, 70 deg C; 2.) H₂O, 70 deg C, 2.5 h

2: 61 percent / pyridine / 2 h / -10 °C

3: 84 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 - 5 °C

4: 2N NaOH / dioxane / 4 h / Ambient temperature

5: 32percent NH₄OH / methanol / 6 h / sealed flask

6: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / -10 - -5 °C

7: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature

8: RED-AL / toluene / 4 h / Ambient temperature

With ammonium hydroxide; sodium hydroxide; potassium tert-butylate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In 1,4-dioxane; pyridine; methanol; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)96541-X

Reference yield:

(2RS,3RS)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide (98769-72-3,98819-72-8) → reboxetine (71620-89-8,71621-36-8,93851-86-6,98769-81-4,98769-83-6,98819-76-2,105017-38-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 32percent NH₄OH / methanol / 6 h / sealed flask

2: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / -10 - -5 °C

3: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature

4: RED-AL / toluene / 4 h / Ambient temperature

With ammonium hydroxide; potassium tert-butylate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In methanol; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)96541-X

upstream raw materials:

(2RS,3RS)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one

2-Ethoxyphenol

benzaldehyde

trans-2,3-epoxy-3-phenylpropan-1-ol

Downstream raw materials:

(S,S)-reboxetine

(2R,3R)-reboxetine

(S,S)-reboxetine (S)-mandelate

(2S,3S)-2-[α-(2-ethoxyphenoxy)benzyl]morpholine succinate

Refernces

• 1、 -. "Sulfoxide ligand metal catalyzed oxidation of olefins". Page/Page column 171. . Retrieved 2019/05/09.
• 2、 Liu, Cheng,Lin, Zhi-Wei,Zhou, Zhao-Hui,Chen, Hong-Bin. "Stereodivergent synthesis of all the four stereoisomers of antidepressant reboxetine". . p. 5395 - 5401. Retrieved 2017/07/10.