20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one → 6alpha,7alpha-Diepoxypregn-4-en-3one

HRID 1708776Notes

Reaction equation

HRID 1708776 reaction equation
O1CCOC1C([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(=CC(=O)[C@@H:18]4[O:27][C@@H:19]42)C=C3)CC1)C.CC1(C)CO[CH:33]([CH:36]([C@@H:38]2[C@:55]3([CH3:56])[C@H:41]([C@H:42]4[C@H:52]([CH2:53][CH2:54]3)[C@:50]3([CH3:51])[C:45](=[CH:46][C:47](=[O:58])[C@@H:48]5[O:57][C@@H:49]53)C=C4)[CH2:40][CH2:39]2)C)OC1>>[O:57]1[C:48]2=[C:49]3[C@:50]([CH3:51])([CH2:45][CH2:46][C:47]2=[O:58])[C@@H:52]2[C@H:42]([C@H:41]4[C@:55]([CH3:56])([CH2:54][CH2:53]2)[C@@H:38]([CH2:36][CH3:33])[CH2:39][CH2:40]4)[C@@H:18]2[O:27][C@:19]123

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 867457986alpha,7alpha-Diepoxypregn-4-en-3oneYield 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,7α-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-cf29bfa3218040feaae7b5f0fcf665a0
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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