20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha, 2alpha-epoxypregna-5,7-dien-3beta-yl acetate → 20-(1,3-Dioxolan-2-yl)-1alpha,2alpha-epoxypregna-5,7-dien-3beta-ol

HRID 1196347Notes

Reaction equation

HRID 1196347 reaction equation
C(O[C@H]1CC[C@@]2(C)C(=CC=C3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C2(C3OCCO3)OC2)C1)(=O)C.C([O:35][C@H:36]1[C@@H:62]2[O:63][C@@H:61]2[C@@:60]2([CH3:64])[C:38](=[CH:39][CH:40]=[C:41]3[C@@H:59]2[CH2:58][CH2:57][C@@:56]2([CH3:65])[C@H:42]3[CH2:43][CH2:44][C@@H:45]2[CH:46]([CH:48]2[O:53][CH2:52]C(C)(C)[CH2:50][O:49]2)[CH3:47])[CH2:37]1)(=O)C>>[O:53]1[CH2:52][CH2:50][O:49][CH:48]1[CH:46]([C@@H:45]1[C@:56]2([CH3:65])[C@H:42]([C:41]3[C@H:59]([CH2:58][CH2:57]2)[C@:60]2([CH3:64])[C:38]([CH2:37][C@@H:36]([OH:35])[C@@H:62]4[O:63][C@@H:61]42)=[CH:39][CH:40]=3)[CH2:43][CH2:44]1)[CH3:47]

Participants

3

Reactant 2

HCID 8674580520-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha, 2alpha-epoxypregna-5,7-dien-3beta-yl acetateHCID 8674582020-(1,3-Dioxolan-2-yl)--epoxypregna-5,7-dien-3beta-yl acetate

Product 1

HCID 8674581920-(1,3-Dioxolan-2-yl)-1alpha,2alpha-epoxypregna-5,7-dien-3beta-olYield 90.1%

Procedure

The procedure of Example 23 was repeated except that 4.5 mg (0.0106 mmole) of 20-(1,3-dioxolan-2-yl)--epoxypregna-5,7-dien-3β-yl acetate was used in lieu of 5 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-5,7-dien-3β-yl acetate to give 3.7 mg of 20-(1,3-dioxolan-2-yl)-1α,2α-epoxypregna-5,7-dien-3β-ol (yield: 90%).

Sources & evidence

ORD record
ord-b7b16da6c075435f9fa37a6d2691746e
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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