Nitroethane → HCID 13012663, compound

Participants

Reaction Conditions

Reaction Steps

Under an inert atmosphere a solution of nitroethane (4.66 g, 4.44 ml, 62.1 mmol) in ether (15 ml) was treated at room temperature with a solution of cyclopent-2-enone (5 g, 5.1 ml, 60.9 mmol) in ether (90 ml) followed by the addition of triethylamine (70.8 mg, 97.6 μl, 700 μmol) and the dropwise addition of phenyl isocyanate (14.8 g, 13.6 ml, 124 mmol). The light yellow solution was stirred at 25° C. during the weekend. For the workup, the off-white suspension was filtered and washed three times with ether. The filtrate was evaporated, then the crude product was triturated in dichloromethane (15 ml), the solid was filtered off and washed with dichloromethane. After evaporation of the orange-colored filtrate the crude product was purified by flash chromatography on silica gel using a gradient of heptane and ethyl acetate=2:1 to 1:2 as the eluent. The rac-(3aR,6aR)-3-methyl-3a,5,6,6a-tetrahydro-cyclopenta[d]isoxazol-4-one (5.95 g, 70% yield) was obtained as yellow liquid. MS: m/z=139 [M]+. In addition, the rac-(3aR,6aS)-3-methyl-3a,4,5,6a-tetrahydro-cyclopenta[d]isoxazol-6-one (0.37 g, 4.3% yield) was obtained as a yellow oil. MS: m/z=139 [M]+.

Provenance & Evidence