Sodium Sulfate → 20-Methylpregna-5,7-diene-1alpha,3beta,21-triol

HRID 1587615Notes

Reaction equation

HRID 1587615 reaction equation
COC([O:5][C@@H:6]1[C@@:28]2([CH3:29])[C:10](=[CH:11][CH:12]=[C:13]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:14]3[CH2:15][CH2:16][C@@H:17]2[CH:18]([C:20](OC)=[O:21])[CH3:19])[CH2:9][C@@H:8]([O:31]C(OC)=O)[CH2:7]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.C(OCC)C>[CH3:19][CH:18]([C@@H:17]1[C@:24]2([CH3:30])[C@H:14]([C:13]3[C@H:27]([CH2:26][CH2:25]2)[C@:28]2([CH3:29])[C:10]([CH2:9][C@@H:8]([OH:31])[CH2:7][C@@H:6]2[OH:5])=[CH:11][CH:12]=3)[CH2:15][CH2:16]1)[CH2:20][OH:21]

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 18652401Methyl 1alpha,3beta-bis(methoxycarbonyloxy)pregna-5,7-diene-20 carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 6778765420-Methylpregna-5,7-diene-1alpha,3beta,21-triolYield 117.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carboxylate (70 mg) was added to a suspension of 10 mg of lithium aluminum hydride in 5 ml of tetrahydrofuran with ice cooling and the mixture was stirred with ice cooling for 30 minutes. The resulting reaction mixture was diluted with diethyl ether and the excess reducing agent was decomposed with a saturated aqueous solution of sodium sulfate. The insoluble matter was filtered off and washed well with ethyl acetate. The filtrate and washings were combined and concentrated. The residue was washed with cold diethyl ether to give 58 mg of 20-methylpregna-5,7-diene-1α,3β,21-triol.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe insoluble matter was filtered off
  3. washwashed well with ethyl acetate
  4. concentrationconcentrated
  5. washThe residue was washed with cold diethyl ether

Sources & evidence

ORD record
ord-c341d2f6ddb34b81bf80f6413866c590
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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