Reaktion #1152889

Reaktionsgleichung

17β-(N-formyl-N-methylamino)-oestra-1,3,5(10)-triene-3,16α-diol

lithium aluminium hydride

→

17β-dimethylamino-oestra-1,3,5(10)-triene-3,16α-diol

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added portionwise
2. 2
   Sonstigethe excess of lithium aluminium hydride was destroyed by careful addition of water
3. 3
   workup.ADDITIONThe mixture was diluted with a 1:1 mixture of tetrahydrofuran-ethylacetate (500 ml)
4. 4
   Temperaturrefluxed for 3 h
5. 5
   FiltrationThe inorganic salts were filtered off
6. 6
   Waschenwashed with tetrahydrofuran-ethylacetate (500 ml; 1:1)
7. 7
   Sonstigethe filtrate was evaporated to dryness
8. 8
   SonstigeThe resultant crude product was crystallised from dichloromethane-methanol

Vorschrift

A suspension of 17β-(N-formyl-N-methylamino)-oestra-1,3,5(10)-triene-3,16α-diol (5.41 g) in tetrahydrofuran (110 ml) was kept at 10° C., while lithium aluminium hydride (5.41 g) was added portionwise. The resultant mixture was refluxed for 5 h., then the excess of lithium aluminium hydride was destroyed by careful addition of water. The mixture was diluted with a 1:1 mixture of tetrahydrofuran-ethylacetate (500 ml) and refluxed for 3 h. The inorganic salts were filtered off and washed with tetrahydrofuran-ethylacetate (500 ml; 1:1) and the filtrate was evaporated to dryness. The resultant crude product was crystallised from dichloromethane-methanol to give pure 17β-dimethylamino-oestra-1,3,5(10)-triene-3,16α-diol as an amorphous solid (3.83 g; 73.9%), m.p. 240°-242° C., [α]D +43.4° (c 1.33 in pyridine).

Quelle