(R)-(+)-3-Chlorostyrene oxide → (1R)-1-(3-chlorophenyl)-2-[3-(3-ethoxycarbonylmethoxyphenyl)cyclohexylamino]ethanol

Participants

Reaction Steps

Ethyl 3-(3-aminocyclohexyl)phenoxyacetate (8.47 g) was dissolved in ethanol (50 ml), and (R)-3-chlorostyrene oxide (4.72 g) was added prior to heating to reflux for 7.5 hours. After allowing the mixture to cool, the solvent was concentrated under reduced pressure to obtain an oily substance which was then separated and purified by silica gel column chromatography (n-hexane:ethyl acetate=1:5), to give 8.15 g of (1R)-1-(3-chlorophenyl)-2-[3-(3-ethoxycarbonylmethoxyphenyl) cyclohexylamino]ethanol (trans-H) (compound of Example 11) as an oily substance (61.8% yield).

Provenance & Evidence