1alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha-(methoxycarbonyl)oxypregna-5,7-dien-3beta-ol

HRID 1196390Notes

Reaction equation

HRID 1196390 reaction equation
[CH3:1][C:2]1([CH3:39])[CH2:7][O:6][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([O:34]C(OC)=O)[CH2:20][C@@H:21]3[O:29][C:30]([O:32][CH3:33])=[O:31])=[CH:16][CH:15]=4)[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1.COC(O[C@@H]1[C@@]2(C)C(=CC=C3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C(C=O)C)C[C@@H](OC(OC)=O)C1)=O>>[CH3:39][C:2]1([CH3:1])[CH2:3][O:4][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([OH:34])[CH2:20][C@@H:21]3[O:29][C:30]([O:32][CH3:33])=[O:31])=[CH:16][CH:15]=4)[CH2:12][CH2:11]2)[CH3:9])[O:6][CH2:7]1

Participants

3

Reactant 2

HCID 543675231alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehydeHCID 6785297120-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta-bis(methoxycarbonyloxy)pregn-5,7-diene

Product 1

HCID 6785291720-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha-(methoxycarbonyl)oxypregna-5,7-dien-3beta-olYield 95.1%

Procedure

The reaction and workup procedures of Example 164 were repeated except that 100 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene was used in lieu of 100 mg of 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde to give 85 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α-(methoxycarbonyl)oxypregna-5,7-dien-3β-ol showing the following physical properties.

Workup

  1. customThe reaction and workup procedures of Example 164

Sources & evidence

ORD record
ord-9d17fdf6944a49099abc30694986fa15
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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