Chlorotrimethylsilane → HCID 70145151, compound

HRID 840177Notes

Reaction equation

HRID 840177 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11]([NH:12][C:13](=[O:21])[CH2:14][CH2:15]1)=[CH:10][C:9]3=[O:22].C([N-]C(C)C)(C)C.[Li+].[CH3:31][Si:32](Cl)([CH3:34])[CH3:33]>C1COCC1>[CH3:31][Si:32]([CH3:34])([CH3:33])[O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11]([N:12]([Si:32]([CH3:34])([CH3:33])[CH3:31])[C:13](=[O:21])[CH2:14][CH2:15]1)=[CH:10][C:9]3=[O:22]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 2724682Lithium diisopropylamideHCID 70145248HCID 70145248, compound

Product 1

HCID 70145151HCID 70145151, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

17β-Hydroxy-4-aza-androst-5-ene-3,7-dione (40.000 g, 131.84 mmol) prepared in Example 18A or otherwise obtained is prepared in solution at −78° C. in dry THF (300 mL). Lithium diisopropylamide solution (2.0 M in heptane/THF/ethylbenzene; 135.0 mL, 270.0 mmol) is added under an inert atmosphere and the deprotonation reaction occurs while stirring at −78° C. over 60 minutes. Trimethylsilyl chloride (35.00 mL, 275.8 mmol) is added, and stirring is continued for an additional 15 minutes and then the solution is allowed to warm to room temperature. After stirring an additional 2 hours, the reaction mixture is filtered through Celite® and the filtrate is evaporated to dryness. The residue is redissolved in ether (500 mL) and the resultant slurry is filtered again through Celite®. The solvent is evaporated to give the title compound.

Workup

  1. customthe deprotonation reaction
  2. stirringstirring
  3. waitis continued for an additional 15 minutes
  4. temperatureto warm to room temperature
  5. stirringAfter stirring an additional 2 hours
  6. filtrationthe reaction mixture is filtered through Celite®
  7. customthe filtrate is evaporated to dryness
  8. dissolutionThe residue is redissolved in ether (500 mL)
  9. filtrationthe resultant slurry is filtered again through Celite®
  10. customThe solvent is evaporated

Sources & evidence

ORD record
ord-11f45c9e604b45a8be4251f709bf8fc2
Source dataset
uspto-grants-2002_04
Patent number
US06365597B1

Reaction notes

Loading…