868686-69-5

Basic information

• Product Name: (2R,3S)-2-[α-(2-ethoxyphenoxy)phenylmethyl]morpholine
• Synonyms: (2R,3S)-2-[α-(2-ethoxyphenoxy)phenylmethyl]morpholine
• CAS NO: 868686-69-5
• Molecular Weight: 313.397
• Mol File: 868686-69-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2R,3S)-2-[α-(2-ethoxyphenoxy)phenylmethyl]morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-2-[α-(2-ethoxyphenoxy)phenylmethyl]morpholine(868686-69-5)
• EPA Substance Registry System: (2R,3S)-2-[α-(2-ethoxyphenoxy)phenylmethyl]morpholine(868686-69-5)

Safety Data

• Hazardous Substances Data: 868686-69-5(Hazardous Substances Data)

Upstream product

• 17199-29-0 (S)-Mandelic acid 
• 94-71-3 2-Ethoxyphenol 
• 1030837-58-1 (2R,3S)-2-(α-hydroxyphenylmethyl)morpholine-4-carboxylic acid t-butyl ester 
• 133187-21-0 Methyl (S)-(+)-α-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-phenylacetate 
• 133187-22-1 (2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 1468-28-6 4-benzoylmorpholine 
• 800407-89-0 (2S,3R)-4-benzyl-2-(hydroxyphenylmethyl)morpholin-3-one 
• 1356958-71-8 {[(2R,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate 
• 1452772-76-7 (2R,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide 
• 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 
• 1452772-66-5 (2S,3S)-1-chloro-3-(2-ethoxyphenoxy)-3-phenylpropan-2-ol 
• 100-58-3 phenylmagnesium bromide 

Relevant articles and documents

Stereodivergent synthesis of all the four stereoisomers of antidepressant reboxetine

Chiral amino alcohol-copper(ii) catalysts Cu-L1c and Cu-ent-L1c were utilized to promote the diastereoselective nitroaldol reactions of chiral aldehydes (S)-3 or (R)-3 with nitromethane, which respectively led to the preferential formation of certain stereoisomer for nitro diol derivatives 4. Using this catalytic protocol, all the four stereoisomers of the antidepressant reboxetine were divergently prepared. The highest overall yield of this synthetic route reached up to 30.5% from aldehyde (S)-3.

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.

Application of amide-stabilized sulfur ylide reactivity to the stereodivergent synthesis of (R,S)- and (S,R)-reboxetine

A simple access to (R,S)- and (S,R)-reboxetine from a single chiral sulfonium salt 4 is reported. This approach, based on a stabilized sulfur ylide-mediated epoxidation, followed by a regioselective opening reaction, enables the preparation of these two p