20-(1,3-Dioxolan-2-yl)-pregna-5,7-diene-1alpha,3beta-diol → 1alpha,3beta-Dihydroxypregna-5,7-diene-20-carbaldehyde

HRID 1708781Notes

Reaction equation

HRID 1708781 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]([OH:28])[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](O)C[C@@H]3O)=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]([OH:28])[CH2:18]1

Participants

3

Reactant 2

HCID 6785292520-(1,3-Dioxolan-2-yl)-pregna-5,7-diene-1alpha,3beta-diolHCID 6785294520-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-5,7-diene-1alpha,3beta-diol

Product 1

HCID 538927811alpha,3beta-Dihydroxypregna-5,7-diene-20-carbaldehydeYield 78%

Procedure

The procedure of Example 25 was repeated except that 3.9 mg (0.010 mole) of 20-(1,3-dioxolan-2-yl)pregna-5,7-diene-1α,3β-diol was used in lieu of 4.3 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-5,7-diene-1α,3β-diol to give 2.7 mg of 1α,3β-dihydroxypregna-5,7-diene-20-carbaldehyde (yield: 78%).

Sources & evidence

ORD record
ord-bce6866921a343b3b952ff62c99e7132
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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