Oxygen → HCID 57215923, compound

HRID 1681812Notes

Reaction equation

[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[O:24]=[O:25]>>[O:24]([C@:4]12[CH2:3][C@@H:2]([OH:1])[CH2:21][CH2:20][C@:19]1([CH3:22])[C@@H:18]1[C@H:7]([C@H:8]3[C@:15]([CH3:23])([CH2:16][CH2:17]1)[C@@H:11]([C:12](=[O:14])[CH3:13])[CH2:10][CH2:9]3)[CH:6]=[CH:5]2)[OH:25]

Participants

Reactant 2

HCID 977Oxygen

HCID 8955Pregnenolone

Product 1

HCID 57215923HCID 57215923, compound

Procedure

3β-Hydroxy-5-pregnen-20-one 1 reacts with singlet oxygen to yield 5α-hydroperoxy-3β-hydroxy-6-pregnene-20-one 2. This hydroperoxide undergoes a rearrangement when in chloroform solution to yield 7α-hydroperoxy-3β-hydroxy-5-pregnene-17-one, 3. Treatment of the hydroperoxide with zinc and acetic acid yields 3β,7α-dihydroxy-5-pregnen-20-one 4. ##STR27##

Sources & evidence

ORD record: ord-cf2b2a93d4284d0c9302bf71625ae1b2
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05175154

Reaction notes

Loading…