Réaction #55610

Équation de réaction

borane

sodium hydroxide

hydrogen peroxide

product

17β-tetrahydropyranyloxy-4-androstene

→

final product

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

Solvants

tetrahydrofuran

water

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   AutreTo 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
   Extractionextracted with ethyl ether
5. 5
   Lavagewashed with water, brine
6. 6
   Autredried
7. 7
   Autreevaporated to an oily crystalline material
8. 8
   LavageThe product was washed with cold methanol
9. 9
   Autrepumped dry
10. 10
    Autreto give 175 mg

Mode opératoire

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.

Source