Reaction #55610

Reaction equation

borane

sodium hydroxide

hydrogen peroxide

product

17β-tetrahydropyranyloxy-4-androstene

→

final product

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

Solvents

tetrahydrofuran

water

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   OtherTo 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
   Washwashed with water, brine
6. 6
   Otherdried
7. 7
   Otherevaporated to an oily crystalline material
8. 8
   WashThe product was washed with cold methanol
9. 9
   Otherpumped dry
10. 10
    Otherto give 175 mg

Procedure

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