20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta,7alpha-tris(methoxycarbonyloxy)pregn-5-ene → 20-(1,3-Dioxolan-2-yl)-3beta-(methoxymethyl)oxypregn-5-ene-1alpha,7alpha-diol

HRID 1196378Notes

Reaction equation

HRID 1196378 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([CH2:16][C@@H:17]([O:31][CH2:32][O:33][CH3:34])[CH2:18][C@@H:19]2[O:27]C(=O)C)=[CH:14][C@H:13]3[O:35]C(OC)=O)[CH2:10][CH2:9]1)[CH3:7].CC1(C)COC(C([C@@H]2[C@]3(C)[C@H]([C@H]4[C@H](CC3)[C@]3(C)C(C[C@@H](OC(OC)=O)C[C@@H]3OC(OC)=O)=C[C@H]4OC(OC)=O)CC2)C)OC1>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([CH2:16][C@@H:17]([O:31][CH2:32][O:33][CH3:34])[CH2:18][C@@H:19]2[OH:27])=[CH:14][C@H:13]3[OH:35])[CH2:10][CH2:9]1)[CH3:7]

Participants

3

Reactant 2

HCID 5714185820-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta,7alpha-tris(methoxycarbonyloxy)pregn-5-eneHCID 6785298620-(1,3-Dioxolan-2-yl)-1alpha-acetoxy-3beta-(methoxymethyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-ene

Product 1

HCID 6785300720-(1,3-Dioxolan-2-yl)-3beta-(methoxymethyl)oxypregn-5-ene-1alpha,7alpha-diolYield 88.3%

Procedure

The reaction and workup procedures of Example 140 were repeated except that 90 mg of 20-(1,3-dioxolan-2-yl)-1α-acetoxy-3β-(methoxymethyl)oxy-7α-(methoxycarbonyl)oxypregn-5-ene was used in lieu of 100 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,3β,7α-tris(methoxycarbonyloxy)pregn-5-ene to give 65 mg of 20-(1,3-dioxolan-2-yl)-3β-(methoxymethyl)oxypregn-5-ene-1α,7α-diol showing the following properties.

Workup

  1. customThe reaction and workup procedures of Example 140

Sources & evidence

ORD record
ord-8f9305fe3ba54dd1abc8a7f60e257667
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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