反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
A mixture of iron(III) oxalate hexahydrate (60.4 mg, 0.125 mmol, 10 equiv) in H2O (50 mL) was stirred 2 hours. The reaction mixture was cooled to 0° C. and air was bubbled through the mixture for 10 minutes. A solution of 10′-fluoroanhydrovinblastine (19a, 10.1 mg, 0.0125 mmol, 1 equiv) in H2O (0.5 mL), aqueous 0.1 N HCl (0.5 mL), and CF3CH2OH (0.1 mL) was transferred by pipette to the mixture and NaBH4 (9.5 mg, 0.25 mmol, 1 equiv) in H2O (1 mL) was added to the mixture at 0° C. The resulting mixture was stirred for 30 minutes before being quenched by addition of 28-30% aqueous NH4OH (10 mL). The mixture was extracted with 10% MeOH in CH2Cl2 and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. PTLC (SiO2, Et3N:MeOH:EtOAc=3:3:97) provided 10′-fluorovinblastine 19b (4.0 mg, 0.0048 mmol, 39%) as a white solid and 10′-fluoroleurosidine (2.7 mg, 0.0033 mmol, 26%).
WORKUP
后处理
- customair was bubbled through the mixture for 10 minutes
- additionwas added to the mixture at 0° C
- stirringThe resulting mixture was stirred for 30 minutes
- custombefore being quenched by addition of 28-30% aqueous NH4OH (10 mL)
- extractionThe mixture was extracted with 10% MeOH in CH2Cl2
- dry with materialthe organic layer was dried over Na2SO4
- concentrationconcentrated under reduced pressure