20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxy-7alpha-methoxycarbonyloxypregn-5-en-3beta-yl acetate → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha, 2alpha-epoxypregna-5,7-dien-3beta-yl acetate

HRID 1196323Notes

Reaction equation

HRID 1196323 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:31]2[O:32][C@@H:30]2[C@@:29]2([CH3:33])[C:7](=[CH:8][C@@H:9](OC(=O)N(C)C)[C@@H:10]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:34])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([CH:17]2[O:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][O:18]2)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].C(O[C@H]1[C@@H]2O[C@@H]2[C@@]2(C)C(=C[C@@H](OC(OC)=O)[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C(C2OCC(C)(C)CO2)C)C1)(=O)C>>[C:1]([O:4][C@H:5]1[C@@H:31]2[O:32][C@@H:30]2[C@@:29]2([CH3:33])[C:7](=[CH:8][CH:9]=[C:10]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:34])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([CH:17]2[O:18][CH2:19][C:20]([CH3:24])([CH3:23])[CH2:21][O:22]2)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 8674580120-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxy-7alpha-methoxycarbonyloxypregn-5-en-3beta-yl acetateHCID 867458047alpha-(N,N-dimethylcarbamoyloxy)-20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregn-5-en-3beta-yl acetate

Product 1

HCID 8674580520-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha, 2alpha-epoxypregna-5,7-dien-3beta-yl acetateYield 44.2%

Procedure

The procedure of Example 17 was repeated except that 44.6 mg (0.0798 mmole) of 7α-(N,N-dimethylcarbamoyloxy)-20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregn-5-en-3β-yl acetate was used in lieu of 43.6 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxy-7α-methoxycarbonyloxypregn-5-en-3β-yl acetate to give 16.6 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-5,7-dien-3β-yl acetate. In addition, 16.0 mg of 7α-(N,N-dimethylcarbamolyoxy)-20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregn-5-en-3β-yl acetate was recovered. The yield of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-5,7-dien-3β-yl acetate was 69% based on consumed 7α-(N,N-dimethylcarbamoyloxy)-20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregn-5-en-3β-yl acetate. The 1H-NMR spectrum of the product 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-5,7-dien-3β-yl acetate was in agreement with that of the 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-5,7-dien-3β-yl acetate obtained in Example 17.

Sources & evidence

ORD record
ord-f005b81076b04b2d9f6e3ac30c592dee
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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