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

HRID 1196392Notes

Reaction equation

HRID 1196392 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: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][CH:13]=3)[CH2:10][CH2:9]1)[CH3:7].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>>[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: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][CH:13]=3)[CH2:10][CH2:9]1)[CH3:7]

Participants

3

Reactant 2

HCID 543675231alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehydeHCID 6785294320-(1,3-Dioxolan-2-yl)-1alpha-acetoxy-3beta-(methoxymethyl)oxypregna-5,7-diene

Product 1

HCID 6785288920-(1,3-Dioxolan-2-yl)-3beta-(methoxymethyl)oxypregna-5,7-dien-1alpha-olYield 79%

Procedure

The reaction and workup procedures of Example 164 were repeated except that 100 mg of 20-(1,3-dioxolan-2-yl)-1α-acetoxy-3β-(methoxymethyl)oxypregna-5,7-diene was used in lieu of 100 mg of 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde to give 72 mg of 20-(1,3-dioxolan-2-yl)-3β-(methoxymethyl)oxypregna-5,7-dien-1α-ol showing the following physical properties.

Workup

  1. customThe reaction and workup procedures of Example 164

Sources & evidence

ORD record
ord-e30c7e99cb3d4f5895f4f05644502a27
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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