17,17-Bis(ethylendioxy)androstan-7-one → HCID 178421203, compound
Reaction equation
[CH2:1]1[CH2:14][O:13][C:8]23[O:9][CH2:10][CH2:11][O:12][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([C:16](=O)[CH2:17][CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:2]1.C1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](C/C(=[N:56]\[OH:57])/C5[C@]4(C)CCCC5)[C@@H]2C3)C)O1>>[CH2:1]1[CH2:14][O:13][C:8]23[O:9][CH2:10][CH2:11][O:12][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15](/[C:16](=[N:56]/[OH:57])/[CH2:17][CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:2]1Participants
3
Procedure
17,17-Bis(ethylendioxy)-7(E)-hydroxyiminoandrostane was prepared in 95% yield from 3,3:17,17-bis(ethylendioxy)androstane-7-one by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-6(E)-hydroxyiminoandrostane (Prepn. 20). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography (SiO2, CH2Cl2/MeOH 9/1). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 10.17 (s, 1H), 3.88-3.70 (m, 8H), 2.89 (m, 1H), 2.23-0.71 (m, 19H), 0.90 (s, 3H), 0.77 (s, 3H).