Reaktion #354826

Reaktionsgleichung

17β-carbamoyl-5α-androst-2-ene

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title compound

Ausbeute 6.4%

17β-Cyano-5α-androst-2-ene

Ausbeute 6.4%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe residue, after removal of the chloroform
2. 2
   workup.ADDITIONwas neutralised by the careful addition of aqueous 10% sodium carbonate (150 ml.)
3. 3
   Temperaturwith cooling
4. 4
   Extraktionextracted with ether
5. 5
   WaschenThe etheral solution was washed with water
6. 6
   Trocknendried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated to a partly crystalline residue which
9. 9
   Waschenafter washing with a small portion of ice-cold ether
10. 10
    Sonstigeafforded a crystalline product (3.34 g.)
11. 11
    SonstigeThe etheral washings were chromatographed on a column (1 inch × 6 inches) of florisil
12. 12
    WaschenElution with petrol (200 ml.)
13. 13
    Sonstigeafforded further product (660 mg.)
14. 14
    SonstigeA sample (300 mg.) was recrystallised from petrol

Vorschrift

A solution of 17β-carbamoyl-5α-androst-2-ene (4.33 g.,) and polyphosphate ester (25.0 g.) in chloroform (250 ml.) was refluxed for 16 hours. The residue, after removal of the chloroform, was neutralised by the careful addition of aqueous 10% sodium carbonate (150 ml.) with cooling and extracted with ether. The etheral solution was washed with water, dried (MgSO4) filtered and evaporated to a partly crystalline residue which, after washing with a small portion of ice-cold ether, afforded a crystalline product (3.34 g.). The etheral washings were chromatographed on a column (1 inch × 6 inches) of florisil. Elution with petrol (200 ml.) afforded further product (660 mg.) gaining a total yield of 4.00 g. A sample (300 mg.) was recrystallised from petrol to afford title compound (260 mg.); m.p. 110°-112°: [α]D + 108°, (c 0.6).

Quelle