(8R,9S,10S,13S,14S)-10-(hydroxymethyl)-13-methyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one → 19-Triphenylsiloxy-5-androsten-17-one

HRID 1390777Notes

Reaction equation

HRID 1390777 reaction equation
OC[C@@]12[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)C(=O)CC4)CC=C1CCCC2.[C:22]1([Si:28]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:29][CH2:30][C@@:31]23[C@@H:48]4[C@H:39]([C@H:40]5[C@@:44]([CH2:46][CH2:47]4)([CH3:45])[C:43](=[O:49])[CH2:42][CH2:41]5)[CH2:38][CH2:37][C:36]2=[CH:35][C:34](=O)[CH2:33][CH2:32]3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:57]1([Si:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:29][CH2:30][C@@:31]23[C@@H:48]4[C@H:39]([C@H:40]5[C@@:44]([CH2:46][CH2:47]4)([CH3:45])[C:43](=[O:49])[CH2:42][CH2:41]5)[CH2:38][CH:37]=[C:36]2[CH2:35][CH2:34][CH2:33][CH2:32]3)[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

Participants

3

Reactant 2

HCID 10334324(8R,9S,10S,13S,14S)-10-(hydroxymethyl)-13-methyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-oneHCID 2280323919-Triphenylsiloxy-4-androstene-3,17-dione

Product 1

HCID 2280690719-Triphenylsiloxy-5-androsten-17-one

Procedure

Substituting 19-hydroxy-5-androsten-17-one for the 19-hydroxy-4-androstene-3,17-dione above results in the formation of 19-triphenylsiloxy-5-androsten-17-one.

Sources & evidence

ORD record
ord-874fa3f68cb744cbb933fd33946bed26
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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