21,21-Dimethoxy-20-methylpregna-5,7-diene-1alpha,3betadiol → 1alpha,3beta-Dihydroxypregna-5,7-diene-20-carbaldehyde

HRID 1196394Notes

Reaction equation

HRID 1196394 reaction equation
C[O:2][CH:3](OC)[CH:4]([CH3:26])[C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12]([CH2:13][C@@H:14]([OH:25])[CH2:15][C@@H:16]2[OH:24])=[CH:11][CH:10]=3)[CH2:7][CH2:6]1.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:24][C@@H:16]1[C@@:17]2([CH3:18])[C:12](=[CH:11][CH:10]=[C:9]3[C@@H:19]2[CH2:20][CH2:21][C@@:22]2([CH3:23])[C@H:8]3[CH2:7][CH2:6][C@@H:5]2[CH:4]([CH:3]=[O:2])[CH3:26])[CH2:13][C@@H:14]([OH:25])[CH2:15]1

Participants

3

Reactant 2

HCID 5718934321,21-Dimethoxy-20-methylpregna-5,7-diene-1alpha,3betadiolHCID 6785297120-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta-bis(methoxycarbonyloxy)pregn-5,7-diene

Product 1

HCID 538927811alpha,3beta-Dihydroxypregna-5,7-diene-20-carbaldehydeYield 51%

Procedure

The reaction and workup procedures of Example 156 were repeated except that 100 mg of 21,21-dimethoxy-20-methyl-pregna-5,7-diene-1α,3β-diol 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 45 mg of 1α,3β-dihydroxypregna-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-d36633b7ae97462f8e4a543c64412826
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

Loading…