174747-08-1

Upstream product

• 171889-13-7 (1S,2R)-1-phenyl-2-<(S)-1-hydroxyethyl>-N,N-diethylcyclopropanecarboxamide 
• 172016-00-1 (1S,2R)-2-Formyl-1-phenyl-cyclopropanecarboxylic acid diethylamide 
• 172015-99-5 (1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide 
• 140-29-4 phenylacetonitrile 
• 63106-93-4 (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 174414-12-1 (1S,4S,5R)-4-methyl-2-oxo-1-phenyl-3-oxabicyclo<3.1.0>hexane 
• 18107-18-1 diazomethyl-trimethyl-silane 

Relevant academic research and scientific papers

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.