Sodium hydride → HCID 68310420, compound

HRID 1021220Notes

Reaction equation

HRID 1021220 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][N:10]([C:17](=[O:20])[CH2:18]Cl)[CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Cl-].[NH4+]>C1COCC1>[O:20]=[C:17]1[N:10]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH2:9][CH2:8][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:21])[CH2:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 68308926HCID 68308926, compound

Product 1

HCID 68310420HCID 68310420, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl{2-[(chloroacetyl)(tetrahydro-2H-pyran-4-yl)amino]ethyl}carbamate (6.86 g) was mixed with THF (70 ml), and sodium hydride (55% suspended in oil) (1.4 g) was added thereto at 0° C., followed by stirring at room temperature overnight. To the reaction mixture was added a saturated aqueous ammonium chloride solution at 0° C., followed by extraction with CHCl3. The organic layer was washed with water and saturated brine, and dried over Na2SO4, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane/MeOH) to obtain tert-butyl 3-oxo-4-(tetrahydro-2H-pyran-4-yl)piperazine-1-carboxylate (5.25 g).

Workup

  1. additionwas added
  2. customat 0° C.
  3. extractionfollowed by extraction with CHCl3
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over Na2SO4
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (EtOAc/hexane/MeOH)

Sources & evidence

ORD record
ord-708b679c466a4b998de20c12db8c3b5a
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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