TBAF tetrahydrofuran → HCID 69629977, compound

HRID 1792227Notes

Reaction equation

HRID 1792227 reaction equation
[Si]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[CH2:28][OH:29])[CH2:12][C@@H:11]([O:30][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C>[OH:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[CH2:28][OH:29])[CH2:12][C@@H:11]([OH:30])[CH2:10]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 69630335HCID 69630335, compound

Product 1

HCID 69629977HCID 69629977, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androsta-5,7-diene (1.0 g), was added a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (11 ml), followed by reflux for 6 hours. After adding ethyl acetate, the reaction mixture was washed with saturated brine, a saturated aqueous sodium bicarbonate solution (twice) and then saturated brine. The organic layer was dried over anhydrous magnesium sulfate, evaporated under reduced pressure to remove the solvent and the thus obtained residue was purified by column chromatography (hexane:ethyl acetate=1:2) to give the titled compound (560 mg).

Workup

  1. temperatureby reflux for 6 hours
  2. washthe reaction mixture was washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customthe thus obtained residue was purified by column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-d4ff8f2783c34484a23ef81f6b6b95cc
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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