115290-79-4

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy- β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates

A simple and convenient method was reported for the preparation of optically active β-hydroxy-β-arylpropionates, δ-hydroxy-δ- aryl-β-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products.

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).

Asymmetric Synthesis of Both Enantiomers of Tomoxetine and Fluoxetine. Selective Reduction of 2,3-Epoxycinnamyl Alcohol with Red-Al.

Both enantiomers of tomoxetine 7a,7b and fluoxetine 8a,8b (as their hydrochloride salts) have been synthetized from cinnamyl alkohol by asymmetric epoxidation, and their absolute configurations have been established.Optimal conditions for regioselective Red-Al reduction at C-2 of 2,3-epoxycinnamyl alcohol are discussed.