19-Methoxy-androst-4-ene-3beta,17beta-diol → 19-Methoxy-1beta-methyl-4-androstene-3beta,17beta-diol diacetate

HRID 371818Notes

Reaction equation

HRID 371818 reaction equation
[CH3:1][O:2][CH2:3][C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C@@H:16]([OH:22])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]1=[CH:8][C@@H:7]([OH:23])[CH2:6][C@H:5]2[CH3:24].[CH3:25][O:26][CH2:27][C@@:28]12[C@@H:45]3[C@H:36]([C@H:37]4[C@@:41]([CH2:43][CH2:44]3)([CH3:42])[C@@H:40]([OH:46])[CH2:39][CH2:38]4)[CH2:35][C@H:34]([CH3:47])[C:33]1=[CH:32][C@@H:31]([OH:48])[CH2:30][CH2:29]2.C[O:50][CH2:51][C@@:52]12[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)[C@@H](O)CC4)CCC1=C[C@@H](O)CC2>>[C:27]([O:23][C@H:7]1[CH2:6][C@@H:5]([CH3:24])[C@@:4]2([CH2:3][O:2][CH3:1])[C:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[O:22][C:51](=[O:50])[CH3:52])=[CH:8]1)(=[O:26])[CH3:28].[C:3]([O:48][C@H:31]1[CH2:30][CH2:29][C@@:28]2([CH2:27][O:26][CH3:25])[C:33]([C@@H:34]([CH3:47])[CH2:35][C@@H:36]3[C@@H:45]2[CH2:44][CH2:43][C@@:41]2([CH3:42])[C@H:37]3[CH2:38][CH2:39][C@@H:40]2[O:46][C:51](=[O:50])[CH3:52])=[CH:32]1)(=[O:2])[CH3:4]

Participants

5

Reactant 3

HCID 5723996919-Methoxy-androst-4-ene-3beta,17beta-diolHCID 7058343819-Methoxy-6alpha-methyl-4-androstene-3beta,17beta-diolHCID 7058594119-Methoxy-1beta-methyl-4-androstene-3beta,17beta-diol

Product 2

HCID 5712265919-Methoxy-1beta-methyl-4-androstene-3beta,17beta-diol diacetateHCID 5712534319-Methoxy-6alpha-methyl-4-androstene-3beta,17beta-diol diacetate

Procedure

Substituting 19-methoxy-1β-methyl-4-androstene-3β,17β-diol and 19-methoxy-6α-methyl-4-androstene-3β,17β-diol in lieu of the 19-methoxyandrost-4-ene-3β,17β-diol above results in the preparation of 19-methoxy-1β-methyl-4-androstene-3β,17β-diol diacetate and 19-methoxy-6α-methyl-4-androstene-3β,17β-diol diacetate.

Sources & evidence

ORD record
ord-e8f43711ab954e73895341d02847d5d7
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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