HCID 19899112, compound → HCID 67895933, compound

Participants

Reaction Steps

1 g (3.13 mmol) of methyl 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-methylene-4H-cyclohept[d]isoxazole-7-carboxylate was dissolved in 60 ml of glacial acetic acid and 0.3 g of 5% platinum-on-carbon catalyst was added under a nitrogen atmosphere. The mixture was shaken in a hydrogen atmosphere at room temperature and under atmospheric pressure for 8 hours. The catalyst was removed by filtration and washed with glacial acetic acid. The filtrate was evaporated and the residue was chromatographed on silica gel using 20% ethyl acetate in hexane for the elution. There were obtained 0.47 g of methyl cis-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-methyl-4H-cyclohept[d]isoxazole-7-carboxylate of melting point 90°-91° C. and 0.45 g of methyl trans-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-methyl-4H-cyclohept[d]isoxazole-7-carboxylate of melting point 108° C.

Provenance & Evidence