Sodium hydride → HCID 21906105, compound

HRID 1246753Notes

Reaction equation

HRID 1246753 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.Cl[C:18]1[CH:23]=[N:22][CH:21]=[CH:20][N:19]=1>CS(C)=O>[N:19]1[CH:20]=[CH:21][N:22]=[CH:23][C:18]=1[O:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 73277ChloropyrazineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21906105HCID 21906105, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a slurry of sodium hydride (about 60% oil suspension, 114 mg) in dimethyl sulfoxide (5 ml) was added dropwise tert-butyl 4-hydroxy-1-piperidinecarboxylate (576 mg). Considerable foaming occurred and the solution turned pale orange. To this solution was added chloropyrazine (377 mg) and the mixture was stirred at room temperature for 12 hours. The resulting mixture was partitioned between saturated aqueous sodium hydrogencarbonate solution and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residual solid was triturated with a mixture of ethyl acetate and n-hexane to give the title compound (472 mg) as white crystals.

Workup

  1. customThe resulting mixture was partitioned between saturated aqueous sodium hydrogencarbonate solution and ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residual solid was triturated with a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-8e8059c8da9e479c940f01ad5947b511
Source dataset
uspto-grants-2006_10
Patent number
US07129243B2

Reaction notes

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