Sodium Bicarbonate → HCID 22248214, compound

HRID 890112Notes

Reaction equation

HRID 890112 reaction equation
[C:1]([O:5][C:6]1[C:7]([CH:12]=O)=[N:8][CH:9]=[CH:10][N:11]=1)([CH3:4])([CH3:3])[CH3:2].[C:14]([C:17]1[CH:30]=[CH:29][CH:28]=[CH:27][C:18]=1[O:19][CH2:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:16])[NH2:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6]1[C:7]([CH2:12][N:24]2[CH2:23][CH2:22][CH:21]([CH2:20][O:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[C:14]([NH2:15])=[O:16])[CH2:26][CH2:25]2)=[N:8][CH:9]=[CH:10][N:11]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 222482803-(tert-Butoxy)pyrazine-2-carbaldehydeHCID 22248369HCID 22248369, compound

Product 1

HCID 22248214HCID 22248214, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 106 mg of 3-tert-butoxypyrazine-2-carboxaldehyde and 105 mg of 4-(2-carbamoylphenoxymethyl)piperidine in 5 ml of dichloromethane, 153 mg of sodium triacetoxyborohydride was added and the mixture was stirred overnight at room temperature. Aqueous sodium bicarbonate solution was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (171 mg, 95% yield).

Workup

  1. additionwas added
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-48b26488c9cf4233bd0dda97ee39fdc6
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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