19-t-Butyldimethylsiloxy-4-androstene-3,17-dione → 19-t-Butyldimethylsiloxy-6alpha-methyl-4-androstene-3,17-dione

HRID 1390768Notes

Reaction equation

HRID 1390768 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][C@H:9]([CH3:22])[C:8]1=[CH:7][C:6](=[O:23])[CH2:5][CH2:4]2.O(C[C@@]12[C@@H]3[C@H]([C@H]4[C@@:46](CC3)(C)[C:45](=[O:51])CC4)CCC1=CC(=O)CC2)[Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>>[O:1]([CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][C@H:9]([CH3:22])[C:8]1=[CH:7][C:6](=[O:23])[CH2:5][CH2:4]2)[Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].[C:45]([OH:51])(=[O:1])[CH3:46].[O:23]([CH:6]1[CH2:7][CH2:8][C@@:3]2([CH2:2][OH:1])[C:4](=[CH:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=[O:21])[CH2:5]1)[Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 1057397419-t-Butyldimethylsiloxy-4-androstene-3,17-dioneHCID 7058392519-Hydroxy-6alpha-methyl-4-androstene-3,17-dione

Product 2

HCID 2280325919-t-Butyldimethylsiloxy-6alpha-methyl-4-androstene-3,17-dioneHCID 1317114283-t-Butyldimethylsiloxy-19-hydroxy-5-androsten-17-one acetate

Procedure

Following essentially the same procedure and substituting 19-hydroxy-6α-methyl-4-androstene-3,17-dione and 3β,19-dihydroxy-5-androsten-17-one 19-acetate for the 19-hydroxy-4-androstene-3,17-dione above results in the preparation of 19-t-butyldimethylsiloxy-6α-methyl-4-androstene-3,17-dione and 3-t-butyldimethylsiloxy-19-hydroxy-5-androsten-17-one acetate, respectively.

Sources & evidence

ORD record
ord-7cd645e76005409d8f763e6cfa22a618
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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