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 1708824Notes

Reaction equation

HRID 1708824 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)[O:4][CH2:3]1.[CH3:36][O:37][C:38]([O:40][C@@H:41]1[C@@:59]2([CH3:60])[C:45](=[CH:46][CH:47]=[C:48]3[C@@H:58]2[CH2:57][CH2:56][C@@:55]2([CH3:61])[C@H:49]3[CH2:50][CH2:51][C@@H:52]2[CH2:53][CH3:54])[CH2:44][C@@H:43]([O:62]C(OC)=O)[CH2:42]1)=[O:39]>>[OH:62][C@H:43]1[CH2:42][C@H:41]([O:40][C:38]([O:37][CH3:36])=[O:39])[C@@:59]2([CH3:60])[C:45](=[CH:46][CH:47]=[C:48]3[C@@H:58]2[CH2:57][CH2:56][C@@:55]2([CH3:61])[C@H:49]3[CH2:50][CH2:51][C@@H:52]2[CH:53]([CH:3]=[O:4])[CH3:54])[CH2:44]1

Participants

3

Reactant 2

HCID 2284392720-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(methoxycarbonyl)oxypregna-5,7-dien-1alpha-olHCID 867482231alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene

Product 1

HCID 867458373beta-Hydroxy-1alpha-(methoxycarbonyl)oxypregna-5,7-diene-20-carbaldehyde

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-dimethoxycarbonyl)oxypregna-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-7092b82ebd9543ed8be84f500b118799
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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