反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
CONDITIONS
反应条件
- 温度
- 55 °C
PROCEDURE
实验过程
To a solution of buprenorphine (1) (10.0 g, 21.58 mMol) in CCl4 (21.7 ml, 224.5 mMol) and THF (200 ml) was added at 0° C. LiAlH4 (320 ml, 1.0 M, 320 mMol) in THF. The reaction mixture was heated to 55° C. for 24 h. The resulting reaction mixture was cooled to 0° C. and the reaction was quenched by slow, portion-wise addition of Na2SO4·10H2O (103 g), followed by addition of EtOAc (400 ml). After 20 minutes agitation, the resulting slurry was filtered through the pre-packed Solka Floc-40 (18 g). The resulting wet cake was washed thoroughly with EtOAc (2×100 ml). The combined filtrate was concentrated to dryness, affording 13.5 g of crude compound 2 which was subsequently purified by column chromatography on silica gel to afford 6.03 g of compound 2 (62.2% yield) as a white solid with a purity of >99%.
WORKUP
后处理
- customThe resulting reaction mixture
- temperaturewas cooled to 0° C.
- customthe reaction was quenched by slow,
- additionportion-wise addition of Na2SO4·10H2O (103 g)
- additionfollowed by addition of EtOAc (400 ml)
- filtrationthe resulting slurry was filtered through the pre-packed Solka Floc-40 (18 g)
- washThe resulting wet cake was washed thoroughly with EtOAc (2×100 ml)
- concentrationThe combined filtrate was concentrated to dryness