115290-79-4

Basic information

• Product Name: (R)-3-(2-methylphenoxy)-3-phenylprop-1-yl methanesulfonate
• Synonyms: (R)-3-(2-methylphenoxy)-3-phenylprop-1-yl methanesulfonate
• CAS NO: 115290-79-4
• Molecular Weight: 320.409
• Mol File: 115290-79-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (R)-3-(2-methylphenoxy)-3-phenylprop-1-yl methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(2-methylphenoxy)-3-phenylprop-1-yl methanesulfonate(115290-79-4)
• EPA Substance Registry System: (R)-3-(2-methylphenoxy)-3-phenylprop-1-yl methanesulfonate(115290-79-4)

Safety Data

• Hazardous Substances Data: 115290-79-4(Hazardous Substances Data)

Upstream product

• 118856-08-9 butyric acid 2-ethoxycarbonyl-1-phenyl-ethyl ester 
• 838841-85-3 (3S) ethyl β-butyryloxy-β-phenyl propionate 
• 5764-85-2 Ethyl 3-hydroxy-3-phenylpropanoate 
• 96854-34-1 (S)-3-phenyl-1,3-propanediol 
• 100-52-7 benzaldehyde 
• 321-98-2 (1S,2R)-(+)-ephedrine 
• 104713-12-4 (R)-1-phenylprop-2-en-1-ol 
• 66583-43-5 (+)N-methyl-ephedrine methiodide 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 77118-87-7 (S)-1-Phenyl-3-buten-1-ol 
• 444575-93-3 (R)-(-)-1-phenyl-1-(2-methylphenoxy)-2-propene 
• 115290-77-2 (1S) 3-phenyl-3-hydroxypropyl methanesulfonate 
• 95-48-7 ortho-cresol 

Downstream Products

• 105314-52-1 (R)-tomoxetine 
• 82248-59-7 atomoxetine hydrochloride 

Relevant articles and documents

An efficient chemoenzymatic route to the antidepressants (R)-fluoxetine and (R)-tomoxetine

(S)-1-Phenyl-3-buten-1-ol (1), prepared in high optical purity by enzymatic resolution of the racemate, is a convenient building block for the synthesis of (R)-fluoxetine (7a) and (R)-tomoxetine (7b). Compound 1 was converted to the title drugs by etherification with appropriate phenols under Mitsunobu conditions, ozonolysis of the terminal double bond, mesylation of the resulting alcohol and substitution with methylamine.

A stereospecific ruthenium-catalyzed allylic alkylation

Good regioselectivity and chirality transfer for aryl-substituted allyl units is achieved in allylic alkylations with a wide range of nucleophiles by using the highly active ruthenium catalyst 1. This method provides a route to antidepressants such as (-)-fluoxetine from (S)-ephedrine (see scheme; Cp* = η5-C5Me5, TBAT = tetrabutylammonium triphenyldifluorosilicate).