Diethyl Pyrocarbonate → HCID 57847220, compound

Participants

Reaction Steps

To a mixture of the compound (242 mg, 0.75 mmol) synthesized in Reference Example 8, (1S*,2R*)-2-(anilinocarbonyl)cyclohexanecarboxylic acid (222 mg, 0.90 mmol) and triethylamine (0.313 ml, 2.25 mmol) in DMF (7.5 ml) was added DEPC (0.151 ml, 0.90 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate solution was added, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (2:1, v/v). The title compound (1R*,2S*,3aR*,4R*,9bR*) (163 mg, 45%) was obtained as a white solid from the first eluted fraction.

Provenance & Evidence