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 1708779Notes

Reaction equation

HRID 1708779 reaction equation
C([O:4][C@H:5]1[C@@H:28]2[O:29][C@@H:27]2[C@@:26]2([CH3:30])[C:7](=[CH:8][CH:9]=[C:10]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([CH:17]2[O:21][CH2:20][CH2:19][O:18]2)[CH3:16])[CH2:6]1)(=O)C.C(O[C@H]1[C@@H]2O[C@@H]2[C@@]2(C)C(=CC=C3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C(C2OCC(C)(C)CO2)C)C1)(=O)C>>[O:18]1[CH2:19][CH2:20][O:21][CH:17]1[CH:15]([C@@H:14]1[C@:22]2([CH3:31])[C@H:11]([C:10]3[C@H:25]([CH2:24][CH2:23]2)[C@:26]2([CH3:30])[C:7]([CH2:6][C@@H:5]([OH:4])[C@@H:28]4[O:29][C@@H:27]42)=[CH:8][CH:9]=3)[CH2:12][CH2:13]1)[CH3:16]

Participants

3

Reactant 2

HCID 8674580520-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha, 2alpha-epoxypregna-5,7-dien-3beta-yl acetateHCID 8674581820-(1,3-Dioxolan-2-yl)-1alpha,2alpha-epoxypregna-5,7-dien-3beta-yl acetate

Product 1

HCID 8674581920-(1,3-Dioxolan-2-yl)-1alpha,2alpha-epoxypregna-5,7-dien-3beta-olYield 90.3%

Procedure

The procedure of Example 23 was repeated except that 4.5 mg (0.0106 mmole) of 20-(1,3-dioxolan-2-yl)-1α,2α-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-e2846f8d5c404def9ebb8b7bf420736c
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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