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
3-[2-(2-Methoxy-phenyl)-ethyl]-2,4-dioxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound 8, 0.77g, 1.82 mmol) was dissolved in methanol (18 mL). The mixture was cooled to 0° C., and NaBH4 (0.14 g, 3.64 mmol) was added in portions from the top. The reaction was stirred for 10 minutes and then carefully quenched with water. MeOH was removed under reduced pressure, and the residue was extracted with EtOAc. The combined organic layers were washed with 10% citric acid (5 mL), water (5 mL), saturated NaHCO3 (5 mL), and brine (5 mL), and finally passed over a short plug of Na2SO4. The solvents were evaporated to give Compound 9 (0.65 g, 83%, mixture of isomers) as a clear oil, which was of sufficiently good quality to be advanced to the next step without further purification. Rf=0.5 (50% EtOAc/hexanes).
WORKUP
后处理
- customcarefully quenched with water
- customMeOH was removed under reduced pressure
- extractionthe residue was extracted with EtOAc
- washThe combined organic layers were washed with 10% citric acid (5 mL), water (5 mL), saturated NaHCO3 (5 mL), and brine (5 mL)
- customThe solvents were evaporated