Potassium bis(trimethylsilyl)amide → HCID 21106151, compound

HRID 1354983Notes

Reaction equation

HRID 1354983 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-916b65ac80b546e4af1ab075f924837f
Source dataset
uspto-grants-2007_05
Patent number
US07223888B2

Reaction notes

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