Tetrabutylammonium Fluoride → HCID 67301512, compound

HRID 1014969Notes

Reaction equation

HRID 1014969 reaction equation
[Si]([O:8][C@@H:9]1[C@@:35]2([CH3:36])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:37])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([O:23][CH2:24][CH2:25][C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[CH3:22])[CH2:12][C@@H:11]([O:38][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:8][C@@H:9]1[C@@:35]2([CH3:36])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:37])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([O:23][CH2:24][CH2:25][C:26]([N:28]([CH3:29])[CH3:30])=[O:27])[CH3:22])[CH2:12][C@@H:11]([OH:38])[CH2:10]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67301504HCID 67301504, compound

Product 1

HCID 67301512HCID 67301512, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-(N,N-dimethylaminocarbonylethoxy)pregna-5,7,16-triene (100 mg, 0.15 mmol) in tetrahydrofuran (6.0 ml), a 1M tetrahydrofuran solution of tetra-n-butylammonium fluoride (1.5 ml) was added and stirred at 50° C. for 1 hour under a nitrogen stream. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed sequentially with 0.5N hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After evaporation under reduced pressure to remove the solvent, the resulting residue was purified by preparative thin layer chromatography (1.0 mm×2 plates, chloroform:methanol=10:1) to give the titled compound (45 mg, 70.3%) as a colorless foam.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed sequentially with 0.5N hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter evaporation under reduced pressure
  5. customto remove the solvent
  6. customthe resulting residue was purified by preparative thin layer chromatography (1.0 mm×2 plates, chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-0cd603a744824e15ab65d57350187a4b
Source dataset
uspto-grants-2011_07
Patent number
US07985744B2

Reaction notes

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