20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one → Diepoxypregn-4-en-3-one

HRID 1196344Notes

Reaction equation

HRID 1196344 reaction equation
[O:1]1CC[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:28])[C@@H:18]4O[C@@H:19]42)[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)C.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@@H]5O[C@@H]53)C=C4)CC2)C)OC1>>[O:3]1[C:6]2([O:1][CH:2]12)[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:28])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 8674579720-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-oneHCID 8674581520-(1,3-Dioxolan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one

Product 1

HCID 131717371Diepoxypregn-4-en-3-oneYield 75%

Procedure

The procedure of Example 7 was repeated except that 0.295 g (0.769 mmole) of 20-(1,3-dioxolan-2-yl)-1α,2α-epoxypregna-4,6-dien-3-one was used in lieu of 0.328 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-4,6-dien-3-one to give 0.231 g of 20-(1,3-dioxolan-2-yl)-1α,2α;6α,760 -diepoxypregn-4-en-3-one (yield: 75%).

Workup

  1. customto give 0.231 g of 20-(1,3-dioxolan-2-yl)-1α,2α

Sources & evidence

ORD record
ord-508f0184a15245d8bed218654d806a08
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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