Reacción #415115

Ecuación de reacción

4-(2-aminoethyl)benzenesulfonamide

sodium cyanoborohydride

5α-androstan-17-one

sodium cyanoborohydride

acetic acid

→

17β-[(2-(4-Aminosulfonylphenyl)ethyl)amino)-5α-androstane Hemihydrate

Disolventes

MeOH

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter a solution was obtained
2. 2
   workup.WAITThe stirring was continued for 19 hours
3. 3
   OtroThe solvent was evaporated from the solution
4. 4
   workup.ADDITIONThe residue was treated with 200 ml of water
5. 5
   Extracciónextracted with CH2Cl2 (3×100 ml
6. 6
   LavadoThe combined extracts were washed with 50 ml of brine
7. 7
   Secadodried over MgSO4
8. 8
   OtroEvaporation of the solvent
9. 9
   workup.WAITleft 3.75 g of solid
10. 10
    OtroThe solid was chromatographed on a 400 g column of silica gel
11. 11
    LavadoThe column was eluted with 10% MeOH
12. 12
    OtroCH2Cl2 and 100 ml fractions were collected
13. 13
    Otrocrystallized from MeOH-H2O giving 0.76 g of the title compound

Procedimiento

A solution of 3.39 g of 4-(2-aminoethyl)benzenesulfonamide in 50 ml of MeOH and 150 ml of THF was acidified with 3 ml (3.15 g) of acetic acid. Then 2.32 g of 5α-androstan-17-one was added. After a solution was obtained, 1.2 g of sodium cyanoborohydride was added. The resulting solution was stirred for 5 hours. An additional 1.2 g of sodium cyanoborohydride was added. The stirring was continued for 19 hours. The solvent was evaporated from the solution. The residue was treated with 200 ml of water, made basic with 50% NaOH solution, and extracted with CH2Cl2 (3×100 ml. The combined extracts were washed with 50 ml of brine and dried over MgSO4. Evaporation of the solvent left 3.75 g of solid. The solid was chromatographed on a 400 g column of silica gel. The column was eluted with 10% MeOH--CH2Cl2 and 100 ml fractions were collected. The fractions were assayed by silica gel TLC (1×4") (10% MeOH--CH2Cl2). Fractions 18-30 were combined and crystallized from MeOH-H2O giving 0.76 g of the title compound.

Fuente