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

Base Information

• Chemical Name: (S,S)-reboxetine (S)-mandelate
• CAS No.: 104968-70-9
• Molecular Formula: C₈H₈O₃*C₁₉H₂₃NO₃
• Molecular Weight: 465.546
• Mol file: 104968-70-9.mol

Synonyms:(S,S)-reboxetine (S)-mandelate

Chemical Property of (S,S)-reboxetine (S)-mandelate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S)-reboxetine (S)-mandelate

There total 15 articles about (S,S)-reboxetine (S)-mandelate 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: 43.0%

(S)-Mandelic acid (17199-29-0) + (+)-(2S,3S)-2-<α-(2-ethoxyphenoxy)benzyl>morpholine methanesulfonate (98819-77-3) → (S,S)-reboxetine (S)-mandelate (104968-70-9)

Guidance literature:

(+)-(2S,3S)-2-<α-(2-ethoxyphenoxy)benzyl>morpholine methanesulfonate; With sodium hydroxide; In dichloromethane; water;

(S)-Mandelic acid; In ethanol;

DOI:10.1021/op200181f

Reference yield: 34.5%

(S)-Mandelic acid (17199-29-0) + (S,S)-reboxetine (71620-89-8,71621-36-8,93851-86-6,98769-81-4,98769-83-6,98819-76-2,105017-38-7) → (S,S)-reboxetine (S)-mandelate (104968-70-9)

Guidance literature:

In ethanol; Large scale reaction;

DOI:10.1021/op200181f

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (S,S)-reboxetine (S)-mandelate (104968-70-9)

Guidance literature:

Multi-step reaction with 6 steps

1: MCPBA / CH₂Cl₂ / 0 deg C, 1.5 h, then RT, 24 h

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

3: 67 percent / pyridine / -10 deg C, 2 h, then RT, 2 h

4: 83 percent / 30percent NH₄OH / N,N-dimethyl-acetamide / Ambient temperature; sealed flask

5: 79 percent / Et₃N / CH₂Cl₂ / 0.5 h / -10 - -5 °C

6: ethanol

With ammonium hydroxide; sodium hydroxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In pyridine; ethanol; dichloromethane; N,N-dimethyl acetamide;

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

upstream raw materials:

(S)-Mandelic acid

(2RS,3SR)-1-chloroacetylamino-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropane

2-Ethoxyphenol

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

Downstream raw materials:

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

Refernces

• 1、 Melloni,Della Torre,Lazzari,et al.. "Configurational studies on 2-[α-(2-ethoxyphenoxy)benzyl]morpholine FCE 20124". . p. 1393 - 1399. Retrieved 2007/10/02.