Reaktion #55610

Reaktionsgleichung

borane

sodium hydroxide

hydrogen peroxide

product

17β-tetrahydropyranyloxy-4-androstene

→

final product

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

Lösungsmittel

tetrahydrofuran

water

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo 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
   Extraktionextracted with ethyl ether
5. 5
   Waschenwashed with water, brine
6. 6
   Sonstigedried
7. 7
   Sonstigeevaporated to an oily crystalline material
8. 8
   WaschenThe product was washed with cold methanol
9. 9
   Sonstigepumped dry
10. 10
    Sonstigeto give 175 mg

Vorschrift

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.

Quelle