20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-5,7-dien-3beta-ol → 21,21-Dimethoxy-20-methylpregna-5,7-diene-1alpha,3betadiol

HRID 1708789Notes

Reaction equation

HRID 1708789 reaction equation
[O:1]1[C@H:3]2[C@H:4]([OH:28])[CH2:5][C:6]3[C@:25]([CH3:26])([C@@H:2]12)[C@@H:24]1[C:9]([C@H:10]2[C@:21]([CH3:27])([CH2:22][CH2:23]1)[C@@H:13]([CH:14]([CH3:20])[CH:15]([O:18][CH3:19])[O:16][CH3:17])[CH2:12][CH2:11]2)=[CH:8][CH:7]=3.CC1(C)COC(C([C@@H]2[C@]3(C)[C@H](C4[C@H](CC3)[C@]3(C)C(C[C@@H](O)[C@@H]5O[C@@H]53)=CC=4)CC2)C)OC1>>[CH3:19][O:18][CH:15]([O:16][CH3:17])[CH:14]([CH3:20])[C@@H:13]1[C@:21]2([CH3:27])[C@H:10]([C:9]3[C@H:24]([CH2:23][CH2:22]2)[C@:25]2([CH3:26])[C:6]([CH2:5][C@@H:4]([OH:28])[CH2:3][C@@H:2]2[OH:1])=[CH:7][CH:8]=3)[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 2284392220-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-5,7-dien-3beta-olHCID 867458261alpha,2alpha-Epoxy-21,21-dimethoxy-20-methylpregna-5,7-dien-3beta-ol

Product 1

HCID 5718934321,21-Dimethoxy-20-methylpregna-5,7-diene-1alpha,3betadiolYield 76.1%

Procedure

The procedure of Example 24 was repeated except that 3.4 mg (0. 00887 mmole) of 1α,2α-epoxy-21,21-dimethoxy-20-methylpregna-5,7-dien-3β-ol was used in lieu of 3.8 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α -epoxypregna-5,7-dien-3β-ol to give 2.6 mg of 21,21-dimethoxy-20-methylpregna-5,7-diene-1α,3β-diol (yield: ca. 75%).

Sources & evidence

ORD record
ord-177e3a313e0f4d8b916189428a014914
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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