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

HRID 1196395Notes

Reaction equation

HRID 1196395 reaction equation
[O:1]1CCO[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:28][CH2:29][O:30][CH3:31])[CH2:18][C@@H:19]2[OH:27])=[CH:14][CH:13]=3)[CH2:10][CH2:9]1)[CH3:7].CC1(C)COC(C([C@@H]2[C@]3(C)[C@H](C4[C@H](CC3)[C@]3(C)C(C[C@@H](OC(OC)=O)C[C@@H]3OC(OC)=O)=CC=4)CC2)C)OC1>>[OH:27][C@@H:19]1[C@@:20]2([CH3:21])[C:15](=[CH:14][CH:13]=[C:12]3[C@@H:22]2[CH2:23][CH2:24][C@@:25]2([CH3:26])[C@H:11]3[CH2:10][CH2:9][C@@H:8]2[CH:6]([CH:2]=[O:1])[CH3:7])[CH2:16][C@@H:17]([O:28][CH2:29][O:30][CH3:31])[CH2:18]1

Participants

3

Reactant 2

HCID 6785288920-(1,3-Dioxolan-2-yl)-3beta-(methoxymethyl)oxypregna-5,7-dien-1alpha-olHCID 6785297120-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta-bis(methoxycarbonyloxy)pregn-5,7-diene

Product 1

HCID 867458361alpha-Hydroxy-3beta-(methoxymethyl)oxypregna-5,7-diene-20-carbaldehydeYield 59%

Procedure

The reaction and workup procedures of Example 156 were repeated except that 100 mg of 20-(1,3-dioxolan-2-yl)-3β-(methoxymethyl)oxypregna-5,7-dien-1α-ol was used in lieu of 100 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene to give 53 mg of 1α-hydroxy-3β-(methoxymethyl)oxypregna-5,7-diene-20-carbaldehyde showing the following physical properties.

Workup

  1. customThe reaction and workup procedures of Example 156

Sources & evidence

ORD record
ord-3c28dc686a92487da6fa0d98a0f185ef
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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