Water → HCID 68807570, compound

HRID 1374783Notes

Reaction equation

HRID 1374783 reaction equation
[OH:1][C@H:2]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:21]2[CH2:20][C@@H:19]([OH:26])[C@@:18]2([CH3:27])[C@@:8]43[O:28][CH:9]4[CH2:10][C@@H:11]2[C:12]2([O:17][CH2:16][CH2:15][O:14]2)[CH3:13])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:1][C@H:2]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:21]2[CH2:20][C@@H:19]([OH:26])[C@@:18]2([CH3:27])[C@:8]3([OH:28])[CH2:9][CH2:10][C@@H:11]2[C:12]2([O:17][CH2:16][CH2:15][O:14]2)[CH3:13])[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86586385HCID 86586385, compound

Product 1

HCID 68807570HCID 68807570, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The 14,15-epoxide (24) (300 mg, 0.77 mmol) in dry tetrahydrofuran (10 ml) is added to a suspension of lithium aluminium hydride (300 mg, 7.89 mmol) in tetrahydrofuran and the reaction refluxed for 48 h. After the addition of water (0.3 ml), sodium hydroxide (15% soln, 0.3 ml) and filtration as described earlier, the mixture is purified by silica gel column chromatography using methanol:chloroform (1:9) as solvent to give the trihydroxy pregnene (25) (250 mg, 83%).

Workup

  1. temperaturethe reaction refluxed for 48 h
  2. filtration0.3 ml) and filtration
  3. customthe mixture is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e36038382a95480f8cebdace955415d2
Source dataset
uspto-grants-2007_01
Patent number
US07166611B2

Reaction notes

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