反应详情

A mixture of 1-ethylcyclopentene (1.0 g, 10.4 mmol) and sodium bicarbonate (0.1 g, 1.19 mmol) in methanol (150 ml) was ozonized at −78° C. until TLC analysis indicated complete consumption of 1-ethylcyclopentene. The crude ozonide was transferred directly to a mixture of 7-amino-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (0.5 g, 3.07 mmol) and 10% palladium on carbon (0.05 g, Degussa type; 50% wet). The flask was fitted with a balloon of hydrogen and allowed to stir for 12 h. The reaction was filtered through GF/F paper and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography eluting with a 10% acetone/hexanes mixture to afford 597 mg (75%) of the title compound.

1. customwas ozonized at −78° C. until TLC analysis
2. customconsumption of 1-ethylcyclopentene
3. filtrationThe reaction was filtered through GF/F paper
4. concentrationthe filtrate concentrated under reduced pressure
5. customThe residue was purified by column chromatography
6. washeluting with a 10% acetone/hexanes mixture