反应详情

Phenyl lithium (33 mL, 60 mmol, 1.8 M solution in dibutyl ether) was mixed in drops with a solution of the title compound from step 1 (5.70 g, 20 mmol) in diethyl ether (60 mL) in argon and at room temperature. During this, the temperature of the reaction solution rose to 35° C. and a solid separated out. The reaction mixture was stirred with reflux for 30 min, then hydrolysed in an ice bath with 20% NH4Cl solution (40 mL) and the organic phase was separated. The aqueous phase was extracted with ether (3×100 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated to low volume in a vacuum. The residue was purified by flash chromatography with chloroform/methanol (20:1→9:1→1:1→1% TEA). The polar diastereomer was obtained in clean form. The non-polar diastereomer was isolated in impure state.

1. customrose to 35° C.
2. customa solid separated out
3. temperaturewith reflux for 30 min
4. customhydrolysed in an ice bath with 20% NH4Cl solution (40 mL)
5. customthe organic phase was separated
6. extractionThe aqueous phase was extracted with ether (3×100 mL)
7. dry with materialThe combined organic phases were dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated to low volume in a vacuum
10. customThe residue was purified by flash chromatography with chloroform/methanol (20:1→9:1→1:1→1% TEA)
11. customThe polar diastereomer was obtained in clean form
12. customThe non-polar diastereomer was isolated in impure state