Sodium bis(trimethylsilyl)amide → HCID 58380065, compound

HRID 404315Notes

Reaction equation

HRID 404315 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:17][N:18]=1)[C:12]([O:14]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[N:18]=[CH:17][C:16]2[CH2:19][CH:20]([C:21]([O:23][CH3:24])=[O:22])[C:12](=[O:14])[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 57467582HCID 57467582, compound

Product 1

HCID 58380065HCID 58380065, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 75 mL dry THF was added methyl 2-(benzyloxy)-5-(3-methoxy-3-oxopropyl)isonicotinate (2.50 g, 7.59 mmol). The temperature of the solution was lowered to −78° C. To this solution was added 1N sodium bis(trimethylsilyl)amide (15.2 mL, 15.2 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) dropwise over 30 minutes. After completion, the reaction was stirred for an hour and then quenched by addition of 25 mL saturated NH4Cl. The organic layer was extracted with EtOAc and washed with 150 mL water and 100 mL brine, and then dried over MgSO4. The organic solvent was evaporated, and the residue was purified by column chromatography with 15% EtOAc/hexane to give desired product H6.4 (1.90 g, 84.1%). MS ESI (pos.) m/e: 298.1 (M+H)+.

Workup

  1. customwas lowered to −78° C
  2. customquenched by addition of 25 mL saturated NH4Cl
  3. extractionThe organic layer was extracted with EtOAc
  4. washwashed with 150 mL water and 100 mL brine
  5. dry with materialdried over MgSO4
  6. customThe organic solvent was evaporated
  7. customthe residue was purified by column chromatography with 15% EtOAc/hexane

Sources & evidence

ORD record
ord-cb65d7349c6f4aa59787db63fa217dc4
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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