반응 #415115

반응 방정식

4-(2-aminoethyl)benzenesulfonamide

sodium cyanoborohydride

5α-androstan-17-one

sodium cyanoborohydride

acetic acid

→

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

용매

MeOH

THF

반응 조건

후처리

1. 1
   기타After a solution was obtained
2. 2
   workup.WAITThe stirring was continued for 19 hours
3. 3
   기타The solvent was evaporated from the solution
4. 4
   workup.ADDITIONThe residue was treated with 200 ml of water
5. 5
   추출extracted with CH2Cl2 (3×100 ml
6. 6
   세척The combined extracts were washed with 50 ml of brine
7. 7
   건조dried over MgSO4
8. 8
   기타Evaporation of the solvent
9. 9
   workup.WAITleft 3.75 g of solid
10. 10
    기타The solid was chromatographed on a 400 g column of silica gel
11. 11
    세척The column was eluted with 10% MeOH
12. 12
    기타CH2Cl2 and 100 ml fractions were collected
13. 13
    기타crystallized from MeOH-H2O giving 0.76 g of the title compound

실험 절차

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.

출처