HCID 12961991, compound → HCID 12961993, compound

Participants

Reaction Steps

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).

Provenance & Evidence