Reaktion #354808

Reaktionsgleichung

17β-cyano-5α-androstan-3-one

isopropanol

triethylamine

→

17β-Cyano-3α-hydroxy- 5α-androstane

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis solution, after being refluxed for 20 hours
2. 2
   Extraktionextracted with chloroform
3. 3
   WaschenThe chloroform solution was washed with water
4. 4
   Trocknendried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated to a gum (1.13 g.)
7. 7
   Wascheneluting successively with ethanol/chloroform (1:49) and ethyl acetate/benzene (1:19)
8. 8
   SonstigeThe main band was removed between the eluant change
9. 9
   Waschenthe final elution
10. 10
    Sonstigebefore removing the main band
11. 11
    Sonstige[α]D + 56° (c 0.4%)

Vorschrift

A solution of 17β-cyano-5α-androstan-3-one (1.0 g.) in the minimum volume of isopropanol (ca. 75 ml.) was added to a stock solution of chloroiridic acid/trimethyl phosphite complex (50 ml.) preneutralised to pH4 with triethylamine (4 ml.). This solution, after being refluxed for 20 hours, was poured into water (200 ml.) and extracted with chloroform. The chloroform solution was washed with water, dried (MgSO4), filtered and evaporated to a gum (1.13 g.). This was subjected to preparative t.l.c. eluting successively with ethanol/chloroform (1:49) and ethyl acetate/benzene (1:19). The main band was removed between the eluant change and the final elution was repeated four times before removing the main band. This gave pure title compound (195 mg.) as a white solid; m.p. 156°-159°; [α]D + 56° (c 0.4%).

Quelle