TBAF tetrahydrofuran → 1alpha,3beta-Dihydroxy-17beta-(4-ethyl-4-hydroxyhexyloxymethyl)androsta-5,7-diene

HRID 1792231Notes

Reaction equation

HRID 1792231 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][CH2:32][C:33]([CH2:44][CH3:45])([O:36][Si](CC)(CC)CC)[CH2:34][CH3:35])[CH2:12][C@@H:11]([O:46][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][CH2:32][C:33]([CH2:34][CH3:35])([OH:36])[CH2:44][CH3:45])[CH2:12][C@@H:11]([OH:46])[CH2:10]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 696305921alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17beta-{4-ethyl-4-(triethylsilyloxy)hexyloxymethyl}androsta-5,7-diene

Product 1

HCID 696301481alpha,3beta-Dihydroxy-17beta-(4-ethyl-4-hydroxyhexyloxymethyl)androsta-5,7-dieneYield 98.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-{4-ethyl-4-(triethylsilyloxy)hexyloxymethyl}androsta-5,7-diene (180 mg), was added a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (6 ml), followed by reflux under heating for 5 hours. After adding ethyl acetate, the mixture was washed with saturated brine, a saturated aqueous sodium bicarbonate solution and then 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 (ethyl acetate) to give the titled compound (0.10 g).

Workup

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

Sources & evidence

ORD record
ord-e72c3fca4eec478aaf6d88c4e7c5a54d
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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