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• W2951344234 abstract "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-diethylcarboxamindes (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." @default.
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• W2951344234 date "1996-01-01" @default.
• W2951344234 modified "2023-09-23" @default.
• W2951344234 title "Synthesis of (+)- and (−)-milnaciprans and their conformationally restricted analogs" @default.
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• W2951344234 doi "https://doi.org/10.1016/0040-4039(95)02221-x" @default.
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