反応 #55610

反応方程式

borane

sodium hydroxide

hydrogen peroxide

product

17β-tetrahydropyranyloxy-4-androstene

→

final product

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

溶媒

tetrahydrofuran

water

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他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
   抽出extracted with ethyl ether
5. 5
   洗浄washed with water, brine
6. 6
   その他dried
7. 7
   その他evaporated to an oily crystalline material
8. 8
   洗浄The product was washed with cold methanol
9. 9
   その他pumped dry
10. 10
    その他to give 175 mg

実験手順

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.

出典