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

HRID 2393208Notes

Reaction equation

HRID 2393208 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[C@H:15](O)[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:22])[CH2:3]1.[O:23]=[O:24]>>[O:23]([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:22])[CH2:10][CH2:9]3)[CH:6]=[CH:5]2)[OH:24]

Participants

3

Reactant 2

HCID 977OxygenHCID 148866313beta,11alpha-Dihydroxy-5-androsten-17-one

Product 1

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

Procedure

3β-Hydroxyandrost-5-en-17-one (DHEA) 1 reacts with singlet oxygen to yield 5α-hydroperoxy-3β-hydroxy-androst-6-en-17-one 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. ##STR35##

Sources & evidence

ORD record
ord-178981b0a35b47e09097779813b06c2d
Source dataset
uspto-grants-1998_09
Patent number
US05804576

Reaction notes

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