1250978-71-2

Basic information

• Product Name: 2-{[(2S,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate
• Synonyms: 2-{[(2S,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate
• CAS NO: 1250978-71-2
• Molecular Weight: 411.476
• Mol File: 1250978-71-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-{[(2S,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-{[(2S,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate(1250978-71-2)
• EPA Substance Registry System: 2-{[(2S,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate(1250978-71-2)

Safety Data

• Hazardous Substances Data: 1250978-71-2(Hazardous Substances Data)

Upstream product

• 109-02-4 4-methyl-morpholine 
• 926-39-6 sulfuric acid mono-(2-amino-ethyl ester) 
• 98769-72-3 (-)-(2S,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide 
• 288-32-4 1H-imidazole 
• 1072-53-3 ethyleneglycol sulfate 
• 98819-73-9 (+)-(2S,3S)-1-amino-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropane 
• 121-44-8 triethylamine 
• 80-70-6 N,N,N',N'-tetramethylguanidine 
• 1340546-28-2 C₁₉H₂₂O₅ 
• 1356958-70-7 C₂₀H₂₄O₇S 
• 98819-70-6 (+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane 
• 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 

Downstream Products

• 71620-89-8 (S,S)-reboxetine 
• 635724-55-9 (2S,3S)-2-[α-(2-ethoxyphenoxy)benzyl]morpholine succinate 

Relevant articles and documents

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.

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.