20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta-bis(methoxycarbonyloxy)pregn-5,7-diene → 1alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde

HRID 1708813Notes

Reaction equation

HRID 1708813 reaction equation
CC1(C)CO[CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([O:34][C:35]([O:37][CH3:38])=[O:36])[CH2:20][C@@H:21]3[O:29][C:30]([O:32][CH3:33])=[O:31])=[CH:16][CH:15]=4)[CH2:12][CH2:11]2)[CH3:9])[O:4]C1>CC(C)=O.S(=O)(=O)(O)O>[CH3:33][O:32][C:30]([O:29][C@@H:21]1[C@@:22]2([CH3:23])[C:17](=[CH:16][CH:15]=[C:14]3[C@@H:24]2[CH2:25][CH2:26][C@@:27]2([CH3:28])[C@H:13]3[CH2:12][CH2:11][C@@H:10]2[CH:8]([CH:5]=[O:4])[CH3:9])[CH2:18][C@@H:19]([O:34][C:35]([O:37][CH3:38])=[O:36])[CH2:20]1)=[O:31]

Participants

4

Reactant 1

HCID 6785297120-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,3beta-bis(methoxycarbonyloxy)pregn-5,7-diene

Product 1

HCID 543675231alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehydeYield 65.3%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 180AcetoneSolvent

Procedure

In 5 ml of acetone was dissolved 100 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,3β-bis(methoxycarbonyloxy)pregn-5,7-diene, followed by addition of one drop of concentrated sulfuric acid, and the mixture was refluxed in an atmosphere of argon gas for 3 hours. The reaction mixture was poured in ice-water and extracted with ether. The extracts were pooled and washed with aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution, followed by concentration under reduced pressure. Finally the concentrate was purified by recrystallization from ether. The procedure yielded 55 mg of 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde showing the following physical properties.

Workup

  1. temperaturethe mixture was refluxed in an atmosphere of argon gas for 3 hours
  2. extractionextracted with ether
  3. washwashed with aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution
  4. concentrationfollowed by concentration under reduced pressure
  5. customFinally the concentrate was purified by recrystallization from ether

Sources & evidence

ORD record
ord-1d2f5fc6722b478095c0cc44622b0cde
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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