C[O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@@H:9]3[CH2:10][CH2:11][C@H:12]1[CH2:21][OH:22].C(O)(=O)C(O)=O>CO.O1CCCC1.O>[OH:22][CH2:21][C@@H:12]1[CH2:11][CH2:10][C@@H:9]2[C@H:8]3[C@H:17]([CH2:16][CH2:15][C@:13]12[CH3:14])[C:18]1[CH2:19][CH2:20][C:3](=[O:2])[CH2:4][C:5]=1[CH2:6][CH2:7]3A solution of (14β,17α)-3-methoxyestra-2,5(10)-diene-17-methanol (Example 1, step iii; 0.30 g) in a mixture of methanol (3 ml) and tetrahydrofuran (2.1 ml) was treated with a solution of oxalic acid (0.105 g) in water (1.8 ml). After 1.5 h stirring at room temperature, the reaction mixture was poured into water and the product was extracted into ethyl acetate. The combined organic phases were washed with a saturated aqueous solution of sodium hydrogencarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (14β,17α)-17-(hydroxymethyl)estr-5(10)-en-3-one (0.20 g), 1H NMR δ 3.77 (m, 1H), 3.52 (t, 1H, J=9.0 Hz), 2.74 (m, 2H), 1.09 (s, 3H).
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