[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@:16]3([C:20]#N)[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[CH2:11][C@H:10]([OH:22])[CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C(=O)(O)[O-:34].[Na+]>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@:16]3([CH:20]=[O:34])[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[CH2:11][C@H:10]([OH:22])[CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1A suspension that consists of 100 mg (0.34 mmol) of 3,16α-dihydroxyestra-1,3,5(10)-triene-9 carbonitrile in 40 ml of toluene is cooled to about −20° C. while being stirred. After 0.9 ml (1.35 mmol) of diisobutylaluminium hydride is added, the reaction is mixed after about 10 minutes with sodium bicarbonate solution, filtered over Celite, and the filtering adjuvant is extracted again with ethyl acetate. The combined organic phases are washed with water. By concentration by evaporation of the solution in a vacuum, 84.6 mg of a light yellow foam is obtained. The product that is contained in the mixture corresponds to a yield of about 52% of theory and is used without further chromatographic working-up in the next stage.
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