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

HRID 1196393Notes

Reaction equation

HRID 1196393 reaction equation
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]3O)=CC=4)CC2)C)OC1.CC1(C)CO[CH:40]([CH:43]([C@@H:45]2[C@:62]3([CH3:63])[C@H:48]([C:49]4[C@H:59]([CH2:60][CH2:61]3)[C@:57]3([CH3:58])[C:52]([CH2:53][C@@H:54]([O:69]C(OC)=O)[CH2:55][C@@H:56]3[O:64][C:65]([O:67][CH3:68])=[O:66])=[CH:51][CH:50]=4)[CH2:47][CH2:46]2)[CH3:44])[O:39]C1>>[OH:69][C@H:54]1[CH2:55][C@H:56]([O:64][C:65]([O:67][CH3:68])=[O:66])[C@@:57]2([CH3:58])[C:52](=[CH:51][CH:50]=[C:49]3[C@@H:59]2[CH2:60][CH2:61][C@@:62]2([CH3:63])[C@H:48]3[CH2:47][CH2:46][C@@H:45]2[CH:43]([CH:40]=[O:39])[CH3:44])[CH2:53]1

Participants

3

Reactant 2

HCID 2284392720-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(methoxycarbonyl)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 867458373beta-Hydroxy-1alpha-(methoxycarbonyl)oxypregna-5,7-diene-20-carbaldehydeYield 74.7%

Procedure

The reaction and workup procedures of Example 156 were repeated except that 100 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-3β-(methoxycarbonyl)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 55 mg of 3β-hydroxy-1α-(methoxycarbonyl)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-ff3fd1e86f314e6e923c87023ab88fc8
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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