Oxygen → 5alpha-Hydroperoxy-3beta-hydroxyandrost-6-en-17one

HRID 1086257Notes

Reaction equation

[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.[O:22]=[O:23]>>[O:22]([C@:4]12[CH2:3][C@@H:2]([OH:1])[CH2:19][CH2:18][C@:17]1([CH3:20])[C@@H:16]1[C@H:7]([C@H:8]3[C@@:12]([CH2:14][CH2:15]1)([CH3:13])[C:11](=[O:21])[CH2:10][CH2:9]3)[CH:6]=[CH:5]2)[OH:23]

Participants

Reactant 2

HCID 977Oxygen

HCID 5881Dehydroepiandrosterone

Product 1

HCID 566283895alpha-Hydroperoxy-3beta-hydroxyandrost-6-en-17one

Procedure

3β-Hyroxyandrost-5-en-17-one (DHEA) 1 reacts with singlet oxygen to yield 5α-hydroperoxy-3β-hydroxyandrost-6-en-17one 2. This hydroperoxide undergoes a rearrangement when in chloroform solution to yield 7α-hydroperoxy-3β-hydroxyandrost-5-en-17-one, 3. Treatment of the hydroperoxide with zinc and acetic acid yields 3β,7α-dihydroxy-androst-5-en-17-one, 4. ##STR43##

Sources & evidence

ORD record: ord-d63fd032945243a9bcf5f77dbfca0f89
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05028631

Reaction notes

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