TBAF tetrahydrofuran → HCID 69629974, compound

HRID 1792233Notes

Reaction equation

HRID 1792233 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][O:29][CH2:30][CH2:31][C:32]([OH:35])([CH3:34])[CH3:33])[CH2:12][C@@H:11]([O:36][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][O:29][CH2:30][CH2:31][C:32]([OH:35])([CH3:34])[CH3:33])[CH2:12][C@@H:11]([OH:36])[CH2:10]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 69630638HCID 69630638, compound

Product 1

HCID 69629974HCID 69629974, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(3-hydroxy-3-methylbutoxymethyl)androsta-5,7-diene (700 mg), was added a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (20 ml), followed by reaction for 6 hours. After adding ethyl acetate, the reaction mixture was washed with saturated brine, a saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, evaporated under reduced pressure to remove the solvent and the resulting residue was purified by column chromatography (dichloromethane: methanol=9:1) to give the titled compound (0.41 g).

Workup

  1. customfollowed by reaction 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 resulting residue was purified by column chromatography (dichloromethane: methanol=9:1)

Sources & evidence

ORD record
ord-a9a7ef79a04e4412a1b1f87986ec6afe
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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