反应详情

温度

0 °C

To a solution of 17D (640 mg, 2.131 mmol), (R)-tetrahydrofuran-3-ol (413 mg, 4.69 mmol) and triphenylphosphine in THF (5 mL) at 0° C., was added diisopropyl azodicarboxylate (0.930 mL, 4.69 mmol) dropwise. The reaction mixture was stirred 0° C. for 30 min, and at rt for 16 h. The mixture was concentrated and purified by flash chromatography (0-50% EtOAc in hexanes). The desired fractions were combined, concentrated. The residue was dissolved in MeOH (10 mL) and THF (2 mL). To this solution was added ammonium chloride (2.250 mL, 63.9 mmol) and zinc (0.195 mL, 21.31 mmol). The mixture was stirred at rt for 2 h, concentrated, stirred with sat. Na2CO3 (50 mL) for 20 min, extracted with EtOAc (3×20 mL). The residue was purified by flash chromatography. The desired fractions were concentrated, dissolved in EtOAc (5 mL), and treated with HCl (4N, 5 mL) for 3 h at rt. The mixture was concentrated to give 39A (630 mg, 2.012 mmol, 94% yield) as a yellow solid. MS (ESI) m/z: 242.2 (M+H)+.

1. waitat rt for 16 h
2. concentrationThe mixture was concentrated
3. custompurified by flash chromatography (0-50% EtOAc in hexanes)
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in MeOH (10 mL)
6. stirringThe mixture was stirred at rt for 2 h
7. concentrationconcentrated
8. stirringstirred with sat. Na2CO3 (50 mL) for 20 min
9. extractionextracted with EtOAc (3×20 mL)
10. customThe residue was purified by flash chromatography
11. concentrationThe desired fractions were concentrated
12. dissolutiondissolved in EtOAc (5 mL)
13. additiontreated with HCl (4N, 5 mL) for 3 h at rt
14. concentrationThe mixture was concentrated