98819-70-6

Basic information

• Product Name: (+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane
• CAS NO: 98819-70-6
• Molecular Weight: 288.343
• Mol File: 98819-70-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane(98819-70-6)
• EPA Substance Registry System: (+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane(98819-70-6)

Safety Data

• Hazardous Substances Data: 98819-70-6(Hazardous Substances Data)

Usage

Description

(+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane, also known as 2-(2-ethoxyphenoxy)-3-phenylpropane, is a chiral molecule with the molecular formula C18H22O2. It has two enantiomers that are non-superimposable mirror images of each other. (+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane is of interest in pharmaceutical research due to its potential therapeutic properties.

Uses

Used in Pharmaceutical Research:
(+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane is used as a potential antihypertensive agent for the development of treatments targeting hypertension. It has been studied for its ability to lower blood pressure and induce relaxation of blood vessels, which can be beneficial in managing high blood pressure and related cardiovascular conditions.
Used in Cardiovascular Condition Treatment:
In addition to its potential as an antihypertensive agent, (+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane is also being investigated for its possible use in treating other cardiovascular conditions. Its effects on blood vessels and blood pressure suggest that it may have broader applications in cardiovascular health, although further research is needed to fully understand its potential impact and efficacy in these areas.

Upstream product

• 1452772-74-5 (2R,3R)-1,2-O-cyclohexylidene-3-acetoxy-3-phenylpropane 
• 1452772-73-4 (1S,2R)-2,3-(cyclohexylidenedioxy)-1-phenylpropan-1-ol 
• 1452772-75-6 (2R,3S)-3-(2-ethoxyphenoxy)-1,2-O-cyclohexylidene-3-phenylpropane 
• 100-58-3 phenylmagnesium bromide 
• 79898-17-2 (2S,3R)-β-phenylglycidic acid 
• 94-71-3 2-Ethoxyphenol 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 104-54-1 3-Phenylpropenol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 40641-81-4 trans-2,3-epoxy-3-phenylpropan-1-ol 

Downstream Products

• 93851-87-7 Reboxetine mesylate 
• 1250978-88-1 C₃₆H₄₃NO₁₀S 
• 635724-55-9 (2S,3S)-2-[α-(2-ethoxyphenoxy)benzyl]morpholine succinate 
• 1250978-71-2 2-{[(2S,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate 
• 1356958-70-7 C₂₀H₂₄O₇S 
• 1452772-66-5 (2S,3S)-1-chloro-3-(2-ethoxyphenoxy)-3-phenylpropan-2-ol 
• 1340546-28-2 C₁₉H₂₂O₅ 
• 98769-71-2 (+)-(2R,3S)-3-(2-ethoxyphenoxy)-2-mesyloxy-1-(4-nitrobenzoyloxy)-3-phenylpropane 
• 71620-89-8 (S,S)-reboxetine 
• 93886-32-9 (-)-(2S,3S)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one 
• 98819-73-9 (+)-(2S,3S)-1-amino-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropane 
• 98769-72-3 (-)-(2S,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide 
• 98769-71-2 (2RS,3SR)-3-(2-ethoxyphenoxy)-2-mesyloxy-1-(4-nitrobenzoyloxy)-3-phenylpropane 
• 105017-38-7 (2R,3R)-reboxetine 

Relevant articles and documents

Regioselective monochloro substitution in carbohydrates and non-sugar alcohols via Mitsunobu reaction: Applications in the synthesis of reboxetine

A regioselective high yielding monochloro substitution (chlorohydrin formation) via Mitsunobu reaction is reported. In carbohydrates and sterically hindered non-sugars, only the primary hydroxyl group is chlorinated, whereas in the non-sugar 1,2- and 1,3-alcohols, predominantly the secondary chloride substitution occurs. The versatile methodology provides indirect access to epoxides with the retention of configuration, as against conventional Mitsunobu reaction which generates epoxides with inversion. The methodology was successfully used as a key step in the synthesis of optically active diastereoisomers of the antidepressant drug reboxetine from (R)-2,3-O- cyclohexylidene-d-glyceraldehyde in ～43% overall yields. The Royal Society of Chemistry.

Process development and scale-up for (±)-reboxetine mesylate

Redevelopment of the commercial process for the synthesis of (±)-reboxetine methanesulfonate is described. An optimized and efficient process for the synthesis of (±)-reboxetine starting from cinnamyl alcohol was developed. The redeveloped process minimizes impurity formation and utilizes simplified processing to substantially improve process yield and throughput, and is suitable for the efficient synthesis of multiton quantities of reboxetine.

Configurational studies on 2-[α-(2-ethoxyphenoxy)benzyl]morpholine FCE 20124

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