Reaktion #1548639

Reaktionsgleichung

sodium cyanoborohydride

sodium cyanoborohydride

sodium hydroxide

3-chloroestra-1,3,5(10)-trien-17-one

3-(trifluoromethyl)benzylamine

→

title compound

Ausbeute 67.1%

3-Chloro-17β-[N-(3-trifluoromethylphenylmethyl)-amino]estra-1,3,5(10)-triene

Ausbeute 67.1%

Lösungsmittel

water

acetic acid

methanol

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONWhen the starting material is dissolved
2. 2
   workup.STIRRINGthe mixture is stirred for another 21 hours
3. 3
   Extraktionextracted with methylene chloride (3×100 ml)
4. 4
   WaschenThe combined extracts are washed with brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Sonstigethe solvent is removed
7. 7
   SonstigeThe product is chromatographed on silica gel
8. 8
   Sonstigerecrystallized in methylene chloride/hexane

Vorschrift

The compound, 3-chloroestra-1,3,5(10)-trien-17-one (2.17 g) is added to a solution of 3-(trifluoromethyl)benzylamine (2.6 g) in methanol (200 ml) and tetrahydrofuran (200 ml) made acidic with acetic acid (1.5 ml). When the starting material is dissolved, sodium cyanoborohydride (0.72 g) is added, the mixture is stirred 24 hours, additional sodium cyanoborohydride (0.7 g) is and the mixture is stirred for another 21 hours. The mixture is diluted with water (200 ml), made basic with 50% sodium hydroxide and extracted with methylene chloride (3×100 ml). The combined extracts are washed with brine, dried over magnesium sulfate and the solvent is removed. The product is chromatographed on silica gel and recrystallized in methylene chloride/hexane to give the title compound (2.26 g).

Quelle