HCID 22806922, compound → HCID 86736335, compound

HRID 1390792Notes

Reaction equation

HRID 1390792 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:22]([CH2:23][CH2:24][C@:6]12[CH3:7])[C@:19]1([CH2:20][OH:21])[C:14]([CH2:15][C@@H:16]([O:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)(=[O:3])[CH3:2].[C:30]([O:33][C@H:34]1[CH2:39][CH2:38][C@H:37]2[C@H:40]3[C@H:51]([CH2:52][CH2:53][C@:35]12[CH3:36])[C@:48]1([CH2:49][OH:50])[C:43]([CH2:44][C@@H:45]([O:54][C:55]2([O:60][CH3:61])[CH2:59][CH2:58][CH2:57][CH2:56]2)[CH2:46][CH2:47]1)=[CH:42][CH2:41]3)(=[O:32])[CH3:31].C(O[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(CO)C(C[C@@H](OCC)CC1)=CC3)(=O)C>>[C:1]([OH:4])(=[O:3])[CH3:2].[OH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:22]([CH2:23][CH2:24][C@:6]12[CH3:7])[C@:19]1([CH:20]=[O:21])[C:14]([CH2:15][C@@H:16]([O:25][Si:26]([CH3:27])([CH3:29])[CH3:28])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3.[C:30]([OH:33])(=[O:32])[CH3:31].[OH:33][C@H:34]1[CH2:39][CH2:38][C@H:37]2[C@H:40]3[C@H:51]([CH2:52][CH2:53][C@:35]12[CH3:36])[C@:48]1([CH:49]=[O:50])[C:43]([CH2:44][C@@H:45]([O:54][C:55]2([O:60][CH3:61])[CH2:59][CH2:58][CH2:57][CH2:56]2)[CH2:46][CH2:47]1)=[CH:42][CH2:41]3

Participants

5

Reactant 3

HCID 22806922HCID 22806922, compoundHCID 22806929HCID 22806929, compoundHCID 70605331HCID 70605331, compound

Product 2

HCID 86736335HCID 86736335, compoundHCID 86736336HCID 86736336, compound

Procedure

Substituting 3β-trimethylsiloxy-5-androstene-17β,19-diol 17-acetate, 3β-(1'-methoxycyclopentyloxy)-5-androstene-17β,19-diol 17-acetate and 3β-(1'-cyclopentenyloxy)-5-androstene-17β,19-diol 17-acetate for the 3β-ethoxy-5-androstene-17β,19-diol 17-acetate above results in the preparation of 17β-hydroxy-3β-trimethylsiloxy-5-androsten-19-one acetate, 17β-hydroxy-3β-(1'-methoxycyclopentyloxy)-5-androsten-19-one acetate and 3β-(1'-cyclopentenyloxy)-17β-hydroxy-5-androsten-19-one acetate, respectively.

Sources & evidence

ORD record
ord-0b75ef29502e46989f1801424003e82e
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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