1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 14333872, compound

HRID 840175Notes

Reaction equation

HRID 840175 reaction equation
[CH2:1]([C@H:3]1[CH:20]=[C:19]2[C@:14]([CH3:22])([CH2:15][CH2:16][C:17](=[O:21])[CH2:18]2)[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([O:23][Si](C(C)(C)C)(C)C)[CH2:7][CH2:6]1)[CH3:2].N12CCCN=C1CCCCC2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[CH2:1]([C@H:3]1[CH2:20][C:19]2[C@:14]([CH3:22])([CH2:15][CH2:16][C:17](=[O:21])[CH:18]=2)[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([OH:23])[CH2:7][CH2:6]1)[CH3:2]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724141Tetrabutylammonium FluorideHCID 70144133HCID 70144133, compound

Product 1

HCID 14333872HCID 14333872, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

7β-Ethyl-17β-tert-butyl-dimethylsilyloxy-androst-5-en-3-one (15.000 g, 34.824 mmol) from Example 16E or otherwise obtained is dissolved in THF (100 mL). To the solution is added 1,8-diazabicyclo[5.4.0]undec-7-ene (1.20 mL, 8.024 mmol) and the reaction mixture is heated to reflux under nitrogen. After 1 hour, the reaction mixture is cooled to room temperature and tetrabutylammonium fluoride (1.0 M in THF; 36.0 mL, 36.00 mmol) is added. The desilylation reaction is allowed to occur over 90 minutes at room temperature with stirring. At the end of this time, the reaction mixture is diluted with EtOAc (500 mL) and washed with saturated aqueous NH4Cl (3×200 mL) and brine (200 mL), then dried over MgSO4, filtered, and evaporated to dryness. The residue is recrystalized from ethanol to give the title compound.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux under nitrogen
  3. customThe desilylation reaction
  4. waitto occur over 90 minutes at room temperature
  5. washwashed with saturated aqueous NH4Cl (3×200 mL) and brine (200 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue is recrystalized from ethanol

Sources & evidence

ORD record
ord-de3fe916c80d401b87e96d1b078aa6ab
Source dataset
uspto-grants-2002_04
Patent number
US06365597B1

Reaction notes

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