反应详情

To a stirred solution of methyl 2-hydroxy-4-(1-tertbutyloxycarbonyl-4-piperidinyloxy)benzoate from Step XX of Example XX (2.50 g, 7.11 mmol) in DMF (50 mL) under N2 was added NaH (427 mg, 10.7 mmol). The reaction mixture was cooled, and allyl bromide (1.23 mL, 14.2 mmol) was added via syringe. The reaction mixture was allowed to warm to ambient temperature and stirred for 2 hours. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and aqueous NaHCO3. The ethyl acetate layer was dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified using pressurized silica gel column chromatography using a gradient elution of 10-15% ethyl acetate in hexanes. Methyl 2-allyloxy-4-(1-tertbutyloxycarbonyl-4-piperidinyloxy)benzoate was obtained as a thick colorless oil.

1. temperatureThe reaction mixture was cooled
2. customThe solvent was removed under reduced pressure
3. customthe residue partitioned between ethyl acetate and aqueous NaHCO3
4. dry with materialThe ethyl acetate layer was dried (MgSO4)
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customThe residue was purified
8. washa gradient elution of 10-15% ethyl acetate in hexanes