Sodium Hydroxide → HCID 22248100, compound

HRID 914900Notes

Reaction equation

HRID 914900 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].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([CH2:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6]1[C:7]([CH2:12][N:27]2[CH2:28][CH2:29][CH:24]([CH2:23][S:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[F:14])=[O:22])[CH2:25][CH2:26]2)=[N:8][CH:9]=[CH:10][N:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 22248093HCID 22248093, compoundHCID 222482803-(tert-Butoxy)pyrazine-2-carbaldehyde

Product 1

HCID 22248100HCID 22248100, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After then dissolving 44 mg of 3-tert-butoxypyrazine-2-carboxaldehyde and 49 mg of the 4-[(2-fluorophenylsulfinyl)methyl]piperidine in 2 ml of dichloromethane, 65 mg of sodium triacetoxyborohydride was added and the mixture was stirred overnight at room temperature. A 1N sodium hydroxide 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 silica gel column chromatography (solvent: ethyl acetate/methanol) to obtain the title compound (43 mg, 52% 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 silica gel column chromatography (solvent: ethyl acetate/methanol)

Sources & evidence

ORD record
ord-d130ba999b9044a3a87e66779c89a0f1
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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