20-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one → 20-(1,3-Dioxolan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one

HRID 1708775Notes

Reaction equation

HRID 1708775 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[CH:18]=[CH:19]2)[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[CH3:7].CC1(C)COC(C([C@@H]2[C@]3(C)[C@H]([C@H]4[C@H](CC3)[C@]3(C)C(=CC(=O)C=C3)C=C4)CC2)C)[O:31]C1>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[C@@H:18]4[O:31][C@@H:19]42)[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[CH3:7]

Participants

3

Reactant 2

HCID 2284393220-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-oneHCID 5406370220-(1,3-Dioxolan-2-yl)pregna-1,4,6-trien-3-one

Product 1

HCID 8674581520-(1,3-Dioxolan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-oneYield 75%

Procedure

The procedure of Example 6 was repeated except that 4.16 g (11.3 mmoles) of 20-(1,3-dioxolan-2-yl)pregna-1,4,6-trien-3-one was used in lieu of 4.66 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one to give 3.25 g of 20-(1,3-dioxolan-2-yl)-1α,2α-epoxypregna-4,6-dien-3-one (yield: 75%).

Sources & evidence

ORD record
ord-c267d7c12ce34bed8bd23eaa06dc5751
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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