98819-76-2

Basic information

• Product Name: Esreboxetine
• Synonyms: (2S)-2-[(S)-(2-ETHOXYPHENOXY)PHENYLMETHYL]MORPHOLINE;esreboxetine;(S,S)-( )-Reboxetine;Morpholine,2-[(S)-(2-ethoxyphenoxy)phenylMethyl]-, (2S)-
• CAS NO: 98819-76-2
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.39
• Mol File: 98819-76-2.mol
• Article Data: 20

Chemical Properties

• Appearance: /
• Density: 1.113
• CAS DataBase Reference: Esreboxetine(CAS DataBase Reference)
• NIST Chemistry Reference: Esreboxetine(98819-76-2)
• EPA Substance Registry System: Esreboxetine(98819-76-2)

Safety Data

• Hazardous Substances Data: 98819-76-2(Hazardous Substances Data)

Usage

Uses

(S,S)-Reboxetine is a stereoisomer of Reboxetine (R142000, Mesylate), a selective noradrenaline reuptake inhibitor.

Upstream product

• 93886-32-9 (2RS,3RS)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one 
• 93886-32-9 (2RS,3SR)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one 
• 93886-32-9 (-)-(2S,3S)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one 
• 918657-06-4 (2S,3S)-4-benzyl-2-[(2-ethoxyphenoxy)phenylmethyl]morpholine 
• 104-54-1 3-Phenylpropenol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 98769-71-2 (2RS,3SR)-3-(2-ethoxyphenoxy)-2-mesyloxy-1-(4-nitrobenzoyloxy)-3-phenylpropane 
• 98819-71-7 (+)-(2R,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-1-(4-nitrobenzoyloxy)-3-phenylpropane 
• 98769-70-1 (2RS,3SR)-3-(2-ethoxyphenoxy)-2-hydroxy-1-(4-nitrobenzoyloxy)-3-phenylpropane 
• 98819-70-6 (+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane 
• 98769-69-8 (2RS,3SR)-3-(2-ethoxyphenoxy)-1,2-dihydroxy-3-phenylpropane 
• 98819-73-9 (+)-(2S,3S)-1-amino-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropane 
• 93851-63-9 (2RS,3RS)-1-amino-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropane 
• 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 
• 104968-70-9 (S,S)-reboxetine (S)-mandelate 
• 635724-55-9 (2S,3S)-2-[α-(2-ethoxyphenoxy)benzyl]morpholine succinate 
• 635724-54-8 2S,3S-2-[α-(2-ethoxyphenoxy)benzyl]morpholine fumarate 
• 98819-77-3 (+)-(2S,3S)-2-<α-(2-ethoxyphenoxy)benzyl>morpholine methanesulfonate 
• 93851-87-7 (2RS,3SR)-2-<α-(2-ethoxyphenoxy)benzyl>morpholine methanesulfonate 
• 93851-87-7 Reboxetine mesylate 

Relevant articles and documents

Synthesis of (S,S)-Reboxetine

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C-H to C-N Cross-Coupling of Sulfonamides with Olefins

Cross-coupling of nitrogen with hydrocarbons under fragment coupling conditions stands to significantly impact chemical synthesis. Herein, we disclose a C(sp3)-N fragment coupling reaction between terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/SOX (sulfoxide-oxazoline) catalyzed intermolecular allylic C-H amination. A range of (56) allylic amines are furnished in good yields (avg. 75%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). Mechanistic studies reveal that the SOX ligand framework is effective at promoting functionalization by supporting cationic π-allyl Pd.

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.