Reaktion #459017

Reaktionsgleichung

sodium hydroxide

potassium carbonate

potassium tri-sec-butylborohydride

17β,19-Dihydroxy-7α-methyl-4-androsten-3-one

hydrogen peroxide

→

7α-methyl-4-androstene-3α,17β,19-triol

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for an additional two hours
2. 2
   Sonstigethe tetrahydrofuran solution decanted
3. 3
   WaschenThe solid residue is washed with fresh tetrahydrofuran
4. 4
   Trocknenthe combined tetrahydrofuran solutions are dried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe filtrate removed by evaporation
7. 7
   SonstigeThe residue is crystallized from acetone

Vorschrift

A 0.5 M solution of potassium tri-sec-butylborohydride in tetrahydrofuran under nitrogen is cooled to -78° C. in a dry ice-acetone bath. 17β,19-Dihydroxy-7α-methyl-4-androsten-3-one in tetrahydrofuran is added slowly and the reaction mixture is stirred for a period of 2 hours at this temperature, warmed to 0° C., and stirred for an additional two hours. The reaction mixture is decomposed by the addition of 3 N sodium hydroxide followed by a 30% hydrogen peroxide solution. Solid potassium carbonate is added and the tetrahydrofuran solution decanted. The solid residue is washed with fresh tetrahydrofuran and the combined tetrahydrofuran solutions are dried over anhydrous sodium sulfate, filtered and the filtrate removed by evaporation. The residue is crystallized from acetone to yield 7α-methyl-4-androstene-3α,17β,19-triol.

Quelle