Potassium Iodide → 3beta-Iodoandrost-5-ene-17-one

HRID 1199152Notes

Reaction equation

HRID 1199152 reaction equation
C([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:28])[CH2:10]1)C1C=CC=CC=1.[I-:29].[K+]>>[OH:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][C@@H:17]([I:29])[C:18]2=[O:28])[CH2:10]1.[I:29][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:28])[CH2:10]1

Participants

4

Reactant 2

HCID 4875Potassium IodideHCID 537649083beta-Benzyloxy-5-androsten-17-one

Product 2

HCID 537259003beta-Iodoandrost-5-ene-17-oneHCID 691041003beta-Hydroxy-16alpha-iodoandrost-5-en-17-one

Procedure

Reaction of 3β,17-dihydroxyandrosta-5,16-diene 17-acetate 1 with mercuric acetate followed by treatment with potassium iodide yields the C-16αiodide which hydrolyses with acid to yield 3β-hydroxy-16α-iodoandrost-5-en-17-one, 2d. Reaction of 2d with silver fluoride yields 3β-hydroxy-16α-fluoroandrost-5-en-17-one, 2a.

Workup

  1. customyields the C-16αiodide which

Sources & evidence

ORD record
ord-ec3cab3b84a44fc6bdcc702501102a66
Source dataset
uspto-grants-1990_02
Patent number
US04898694

Reaction notes

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