93886-32-9

Basic information

• Product Name: 3-Morpholinone, 6-[(2-ethoxyphenoxy)phenylmethyl]-
• CAS NO: 93886-32-9
• Molecular Formula: C19H21NO4
• Molecular Weight: 327.38
• Mol File: 93886-32-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 3-Morpholinone, 6-[(2-ethoxyphenoxy)phenylmethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Morpholinone, 6-[(2-ethoxyphenoxy)phenylmethyl]-(93886-32-9)
• EPA Substance Registry System: 3-Morpholinone, 6-[(2-ethoxyphenoxy)phenylmethyl]-(93886-32-9)

Safety Data

• Hazardous Substances Data: 93886-32-9(Hazardous Substances Data)

Upstream product

• 98769-73-4 (2RS,3SR)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenyl-1-tosyloxypropane 
• 94-71-3 2-Ethoxyphenol 
• 40641-81-4 trans-2,3-epoxy-3-phenylpropan-1-ol 
• 98769-72-3 (2RS,3RS)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide 
• 93851-63-9 (2RS,3RS)-1-amino-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropane 
• 98769-69-8 (2RS,3SR)-3-(2-ethoxyphenoxy)-1,2-dihydroxy-3-phenylpropane 
• 98769-70-1 (2RS,3SR)-3-(2-ethoxyphenoxy)-2-hydroxy-1-(4-nitrobenzoyloxy)-3-phenylpropane 
• 98769-71-2 (2RS,3SR)-3-(2-ethoxyphenoxy)-2-mesyloxy-1-(4-nitrobenzoyloxy)-3-phenylpropane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 93853-04-4 (2RS,3RS)-1-amino-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropane methanesulfonate 
• 104-54-1 3-Phenylpropenol 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 79898-17-2 (2S,3R)-β-phenylglycidic acid 
• 98769-72-3 (-)-(2S,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide 

Downstream Products

• 71620-89-8 (S,S)-reboxetine 
• 105017-38-7 (2R,3R)-reboxetine 
• 635724-55-9 (2S,3S)-2-[α-(2-ethoxyphenoxy)benzyl]morpholine succinate 
• 93851-87-7 Reboxetine mesylate 
• 93851-86-6 reboxetine 
• 93851-85-5 2-[(2-Ethoxy-phenoxy)-phenyl-methyl]-morpholine; hydrochloride 
• 71620-89-8 reboxetine 
• 71620-89-8 (2RS,3SR)-2-<α-(2-ethoxyphenoxy)benzyl>morpholine 

Relevant articles and documents

Synthesis of (S,S)-Reboxetine

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Commercial synthesis of (S,S)-reboxetine succinate: A journey to find the cheapest commercial chemistry for manufacture

The development of a synthetic process for (S,S)-reboxetine succinate, a candidate for the treatment of fibromylagia, is disclosed from initial scale-up to deliver material for registrational stability testing through to commercial route evaluation and subsequent nomination. This entailed evaluation of several alternative routes to result in what would have been a commercially attractive process for launch of the compound.

Process development for (S,S)-reboxetine succinate via a sharpless asymmetric epoxidation

Reboxetine mesylate is a selective norepinephrine uptake inhibitor (NRI) currently marketed as the racemate. The (S,S)-enantiomer of reboxetine is being evaluated for the treatment of neuropathic pain and a variety of other indications. (S,S)-Reboxetine has usually been prepared by resolution of the racemate as the (-)-mandelate salt, an inherently inefficient process. A chiral synthesis starting with a Sharpless asymmetric epoxidation of cinnamyl alcohol to yield (R,R)-phenylglycidol was developed. (R,R)-Phenylglycidol was reacted without isolation with 2-ethoxyphenol to give 4, which was isolated by direct crystallization. Key process variables for the asymmetric epoxidation were investigated. Conversion of (R,S)-4 to reboxetine parallels the racemic synthesis with streamlined and optimized processing conditions. (S,S)-Reboxetine free base was converted directly to the succinate salt without isolation as the mesylate salt.