20-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one → 1alpha,2alpha-Epoxy-3-oxopregna-4,6-diene-20-carbaldehyde

HRID 1196330Notes

Reaction equation

HRID 1196330 reaction equation
CC1(C)CO[CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17](=[CH:18][C:19](=[O:30])[C@@H:20]5[O:29][C@@H:21]53)[CH:16]=[CH:15]4)[CH2:12][CH2:11]2)[CH3:9])[O:4]C1.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)OC1>>[O:29]1[C@H:20]2[C:19](=[O:30])[CH:18]=[C:17]3[C@:22]([CH3:23])([C@@H:21]12)[C@@H:24]1[C@H:14]([C@H:13]2[C@:27]([CH3:28])([CH2:26][CH2:25]1)[C@@H:10]([CH:8]([CH:5]=[O:4])[CH3:9])[CH2:11][CH2:12]2)[CH:15]=[CH:16]3

Participants

3

Reactant 2

HCID 2284393220-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-oneHCID 8674579720-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one

Product 1

HCID 228438831alpha,2alpha-Epoxy-3-oxopregna-4,6-diene-20-carbaldehydeYield 60.2%

Procedure

The procedure of Example 26 was repeated except that 0.426 g (1.0 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-4,6-dien-3-one was used in lieu of 0.410 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one to give 0.205 g of 1α, 2α-epoxy-3-oxopregna-4,6-diene-20-carbaldehyde (yield: 60%).

Sources & evidence

ORD record
ord-3e0995e51c9a40bd8de8722993a1d4cf
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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