反应详情

A mixture of 18a (5.00 g, 16.6 mmole), NaHCO3 (2.90 g, 34.6 mmole) and cyclopropylmethyl bromide (2.80 g, 20.8 mmole) in DMF (50 ml) was heated at 100° under argon for 2 hours. The mixture was cooled, filtered from insoluble material and the filtrate evaporated in high vacuum. The residue was dissolved in dilute NH4OH and extracted with three portions of toluene. The toluene was evaporated to give 4.89 g (83%) of crystalline 19a-CPM. Two recrystallizations from ethanol gave analytically pure 19a-CPM, mp 176.5°-178°. NMR: δ 6.56, s, 2H (aromatic); 6.17, S, 1H, (hydroxy proton); 4.23, d, 1H, (H-5α, J=12.5 Hz); 3.78 (CH3O--); 1.30, d, (H-5β); 0.87, d, 3H (7α-CH3, J=6.5 Hz),

1. temperaturewas heated at 100° under argon for 2 hours
2. temperatureThe mixture was cooled
3. filtrationfiltered from insoluble material
4. customthe filtrate evaporated in high vacuum
5. dissolutionThe residue was dissolved in dilute NH4OH
6. extractionextracted with three portions of toluene
7. customThe toluene was evaporated
8. customto give 4.89 g (83%) of crystalline 19a-CPM
9. customTwo recrystallizations from ethanol
10. customgave analytically pure 19a-CPM, mp 176.5°-178°