171889-13-7

Basic information

• Product Name: (1S,2R)-1-phenyl-2-<(S)-1-hydroxyethyl>-N,N-diethylcyclopropanecarboxamide
• Synonyms: (1S,2R)-1-phenyl-2-<(S)-1-hydroxyethyl>-N,N-diethylcyclopropanecarboxamide
• CAS NO: 171889-13-7
• Molecular Weight: 261.364
• Mol File: 171889-13-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1S,2R)-1-phenyl-2-<(S)-1-hydroxyethyl>-N,N-diethylcyclopropanecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-1-phenyl-2-<(S)-1-hydroxyethyl>-N,N-diethylcyclopropanecarboxamide(171889-13-7)
• EPA Substance Registry System: (1S,2R)-1-phenyl-2-<(S)-1-hydroxyethyl>-N,N-diethylcyclopropanecarboxamide(171889-13-7)

Safety Data

• Hazardous Substances Data: 171889-13-7(Hazardous Substances Data)

Upstream product

• 140-29-4 phenylacetonitrile 
• 172015-99-5 (1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide 
• 63106-93-4 (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 75-16-1 methylmagnesium bromide 
• 172016-00-1 (1S,2R)-2-Formyl-1-phenyl-cyclopropanecarboxylic acid diethylamide 
• 63106-93-4 1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one 

Downstream Products

• 174414-12-1 (1S,4S,5R)-4-methyl-2-oxo-1-phenyl-3-oxabicyclo<3.1.0>hexane 
• 171889-15-9 (1S,2R)-1-phenyl-2-<(S)-1-azidoethyl>-N,N-diethylcyclopropanecarboxamide 
• 171889-17-1 (1S,2R)-1-phenyl-2-acetyl-N,N-diethylcyclopropanecarboxamide 
• 171889-06-8 1-phenyl-2-[(S)-1-aminoethyl]-N,N-diethylcyclopropanecarboxamide 
• 172015-89-3 (1S,2R)-2-((R)-1-Amino-ethyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide 
• 172016-01-2 (1S,2R)-1-phenyl-2-<(R)-1-hydroxyethyl>-N,N-diethylcyclopropanecarboxamide 
• 172016-03-4 (1S,2R)-1-phenyl-2-<(R)-1-azidoethyl>-N,N-diethylcyclopropanecarboxamide 
• 174747-08-1 (1S,2R)-2-((S)-1-Hydroxy-ethyl)-1-phenyl-cyclopropanecarboxylic acid methyl ester 
• 1026741-90-1 Trifluoro-acetic acid (S)-1-((1R,2S)-2-diethylcarbamoyl-2-phenyl-cyclopropyl)-ethyl ester 

Relevant articles and documents

Synthesis of (+)- and (-)-milnaciprans and their conformationally restricted analogs

Reaction of (R)-epichlorohydrin [(R)-5] and phenylacetonitrile (6) in the presence of NaNH2 in benzene gave a cyclopropane derivative which was isolated as lactone 4 [(1S,2R)-2-oxo-1-phenyl-3-oxabicyclo[3,1,0]hexane] of 96% e.e. in 67% yield, after alkaline hydrolysis of the cyano group. Compound 4 was readily converted to (+)-milnacipran [(+)-1], by which the absolute stereochemistry of (+)-1 was confirmed. (1S,2R)-1-phenyl-2-[(S)-1-aminoethyl]-cyclopropane-N,N-diethylcarboxam ides (2), a conformationally restricted analog of 1, was also synthesized in high enantiomeric purity from 4. Starting from (S)-epichlorohydrin [(S)-5], their corresponding enantiomers, namely (-)-milnacipran [(-)-1] and ent-2, were also synthesized.