反应 #55610

反应方程式

borane

sodium hydroxide

hydrogen peroxide

product

17β-tetrahydropyranyloxy-4-androstene

→

final product

17β-tetrahydropyranyloxy-4β-hydroxy-5α-androstane

溶剂

tetrahydrofuran

water

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   其他To a cooled solution (0° C.) of 5 ml
2. 2
   workup.ADDITIONtreated with 5 ml
3. 3
   workup.STIRRINGThe solution was stirred for 1 hr
4. 4
   萃取extracted with ethyl ether
5. 5
   洗涤washed with water, brine
6. 6
   其他dried
7. 7
   其他evaporated to an oily crystalline material
8. 8
   洗涤The product was washed with cold methanol
9. 9
   其他pumped dry
10. 10
    其他to give 175 mg

实验过程

To a cooled solution (0° C.) of 5 ml. of 1 M borane in tetrahydrofuran in 2.7 ml. of dry tetrahydrofuran was added 500 mg. (1.4 millimole) of the product of Step C. in 2.0 ml. of dry tetrahydrofuran. The clear solution was stirred for 1 hr. at room temperature and then cooled to 0° C. and treated with 5 ml. of 2.5 N sodium hydroxide followed by 4 ml. of 30% hydrogen peroxide. The solution was stirred for 1 hr. at room temperature, diluted with water and extracted with ethyl ether, washed with water, brine, dried and evaporated to an oily crystalline material. The product was washed with cold methanol and pumped dry to give 175 mg. of final product having a m.p. of 167°-170° C.

来源