Aldosterone → 18-Hydroxycorticosterone

HRID 1679687Notes

Reaction equation

HRID 1679687 reaction equation
C=C[C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(=CC(=O)C=C2)CC3)CC1.[CH3:23][C@@:24]12[C@H:34]3[C@@H:35]([OH:48])[CH2:36][C@:37]4([CH:46]=[O:47])[C@@H:41]([C:42]([CH2:44][OH:45])=[O:43])[CH2:40][CH2:39][C@H:38]4[C@@H:33]3[CH2:32][CH2:31][C:30]1=[CH:29][C:27](=[O:28])[CH2:26][CH2:25]2>>[CH3:23][C@@:24]12[C@H:34]3[C@@H:35]([OH:48])[CH2:36][C@:37]4([CH2:46][OH:47])[C@@H:41]([C:42]([CH2:44][OH:45])=[O:43])[CH2:40][CH2:39][C@H:38]4[C@@H:33]3[CH2:32][CH2:31][C:30]1=[CH:29][C:27](=[O:28])[CH2:26][CH2:25]2

Participants

3

Reactant 2

HCID 5839AldosteroneHCID 13034987Pregna-1,4,20-trien-3-one

Product 1

HCID 1122218-Hydroxycorticosterone

Procedure

Commercially available 1,4-pregnendiene-3-one was incubated with aldosterone-producing adrenal tissue and Δ1 18-hydroxycorticosterone isolated chromatographically. The diol was then converted to the 11β,18-oxido derivative by refluxing for 30 minutes in ethylene dichloride containing p-toluenesulfonic acid in the same manner described in connection with Example 1 above.

Sources & evidence

ORD record
ord-13cfec00806c48c5a04146382ec77c9c
Source dataset
uspto-grants-1978_03
Patent number
US04081538

Reaction notes

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