20-(5,5-Dimethyl-1,3-dioxan-2-yl)-7alpha-hydroxypregna-1,4-dien-3one → 21,21-Dimethoxy-20-methylpregna-1,4,6-trien-3-one

HRID 1196350Notes

Reaction equation

HRID 1196350 reaction equation
O[C@@H:2]1[CH2:25][C:24]2[C@:19]([CH3:27])([CH:20]=[CH:21][C:22](=[O:26])[CH:23]=2)[C@@H:18]2[C@@H:3]1[C@H:4]1[C@:15]([CH3:28])([CH2:16][CH2:17]2)[C@@H:7]([CH:8]([CH3:14])[CH:9]([O:12][CH3:13])[O:10][CH3:11])[CH2:6][CH2:5]1.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[C@H]4O)CC2)C)OC1>>[CH3:13][O:12][CH:9]([O:10][CH3:11])[CH:8]([CH3:14])[C@@H:7]1[C@:15]2([CH3:28])[C@H:4]([C@H:3]3[C@H:18]([CH2:17][CH2:16]2)[C@:19]2([CH3:27])[C:24](=[CH:23][C:22](=[O:26])[CH:21]=[CH:20]2)[CH:25]=[CH:2]3)[CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 2284393020-(5,5-Dimethyl-1,3-dioxan-2-yl)-7alpha-hydroxypregna-1,4-dien-3oneHCID 540878427alpha-Hydroxy-21,21-dimethoxy-20-methylpregna-1,4-dien-3-one

Product 1

HCID 5391922421,21-Dimethoxy-20-methylpregna-1,4,6-trien-3-oneYield 84%

Procedure

The procedure of Example 5 was repeated except that 2.50 g (6.44 mmoles) of 7α-hydroxy-21,21-dimethoxy-20-methylpregna-1,4-dien-3-one was used in lieu of 3.00 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-7α-hydroxypregna-1,4-dien-3-one to give 2.00 g of 21,21-dimethoxy-20-methylpregna-1,4,6-trien-3-one (yield: 84%).

Sources & evidence

ORD record
ord-094434c527ac4a0b976e9b3ed85a6d38
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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