Chloroform → (1R,5S,6R,7R)-3,3-Ethylenedioxy-7-hydroxy-6-ethoxycarbonylbicyclo[3.3.0]octane

Participants

Reaction Steps

To a stirred solution of 2.09 g of (1S,5R)-7,7-ethylenedioxy-2-ethoxycarbonylbicyclo[3.3.0]octan-3-one (I)' having [α]D21 +23.9° (c=2.55, CHCl3) in 21 ml of ethanol was added at -40° C. over 30 minutes 0.17 g of sodium borohydride. The mixture was stirred for 1 hour. After removal of ethanol in vacuo, the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (eluting solution: 20-50% (v/v) diethyl ether/n-hexane) to obtain 1.60 g of the oily title compound.

Provenance & Evidence