[CH:1]1([O:4][C@H:5]2[CH2:10][CH2:9][C@H:8]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:6]23[CH3:7])[C@:19]2([CH3:20])[C:14]([CH2:15][C@@H:16]([OH:24])[CH2:17][CH2:18]2)=[CH:13][CH2:12]4)[CH2:3][CH2:2]1.C(OC(=O)C)(=O)C.N1C=CC=CC=1.[C:38]([O:41][C@H:42]1[CH2:59][CH2:58][C@@:57]2([CH3:60])[C:44](=[CH:45][CH2:46][C@@H:47]3[C@@H:56]2[CH2:55][CH2:54][C@@:52]2([CH3:53])[C@H:48]3[CH2:49][CH2:50][C@@H:51]2[O:61][CH:62]2[CH2:64][CH2:63]2)[CH2:43]1)(=[O:40])[CH3:39]>O>[CH:6]1([CH2:7][CH2:39][C:38]([O:41][C@H:42]2[CH2:59][CH2:58][C@@:57]3([CH3:60])[C:44](=[CH:45][CH2:46][C@@H:47]4[C@@H:56]3[CH2:55][CH2:54][C@@:52]3([CH3:53])[C@H:48]4[CH2:49][CH2:50][C@@H:51]3[O:61][CH:62]3[CH2:64][CH2:63]3)[CH2:43]2)=[O:40])[CH2:8][CH2:9][CH2:10][CH2:5]1.[C:57]1([CH2:58][CH2:59][C:42]([O:24][C@H:16]2[CH2:17][CH2:18][C@@:19]3([CH3:20])[C:14](=[CH:13][CH2:12][C@@H:11]4[C@@H:21]3[CH2:22][CH2:23][C@@:6]3([CH3:7])[C@H:8]4[CH2:9][CH2:10][C@@H:5]3[O:4][CH:1]3[CH2:2][CH2:3]3)[CH2:15]2)=[O:41])[CH:44]=[CH:45][CH:46]=[CH:47][CH:56]=117β-(Cyclopropyloxy)androst-5-en-3β-ol is treated with acetic anhydride and pyridine. The mixture is poured into water and extracted with ethyl acetate. The ethyl acetate layer is separated and dried and the solvent is evaporated to leave as a residue, 3β-acetyloxy-17β-(cyclopropyloxy)androst-5-ene. 3β-(Cyclopentanepropionyloxy)-17β-(cyclopropyloxy)androst-5-ene and 3β-(benzenepropionyloxy)-17β-(cyclopropyloxy)androst-5-ene are obtained in a similar way using the appropriate acid chlorides.
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