Potassium bis(trimethylsilyl)amide → HCID 21106151, compound

HRID 2357693Notes

Reaction equation

HRID 2357693 reaction equation
C([O:5][C:6](=[O:26])[NH:7][CH:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:16]=1)[CH2:9][CH:10](O)[CH:11]=[CH2:12])(C)(C)C.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1.CCOCC>[C:22]([O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:8]2[CH2:9][CH:10]([CH:11]=[CH2:12])[O:26][C:6](=[O:5])[NH:7]2)=[CH:20][CH:19]=1)([CH3:23])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 68639835HCID 68639835, compound

Product 1

HCID 21106151HCID 21106151, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 46 (20.0 mg, 0.056 mmol) in dry THF (1.2 mL) under N2 at room temperature was added KHMDS solution (0.5 M, 0.12 mL, 0.060 mmol). After the addition, the reaction mixture was stirred for 45 min. and diluted with ether. The solution was washed with 1 N HCl (aq), H2O, saturated NaHCO3 (aq), and brine and dried over Na2SO4. The solvent as removed under reduced pressure and the residue was purified by flash chromatography (hexanes:ethyl acetate 2:1) to afford 47 as a pale yellow oil.

Workup

  1. additionAfter the addition
  2. washThe solution was washed with 1 N HCl (aq), H2O, saturated NaHCO3 (aq), and brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent as removed under reduced pressure
  5. customthe residue was purified by flash chromatography (hexanes:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-7e1dd1d241c4499ea625754c090ca366
Source dataset
uspto-grants-2010_07
Patent number
US07759514B2

Reaction notes

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